Abstract
Progress in the chemistry of compounds having π-conjugated selenaheterocyclic systems is presented. The review concentrates on the most representative selenaheterocycles: selenophene, selenazoles, selenadiazoles, as well as on seleninium salts. Their aromaticity is discussed and the chemical properties are illustrated by the most characteristic reactions. Various approaches to the synthesis of different selenaaromatic ring systems are presented. A number of selenaaromatic compounds and their nonconjugated analogs are indicated as reagents and catalysts for organic synthesis, as biological response modifiers of practical importance as pharmaceuticals, and as new materials for electronics.
Abbreviations
- AIBN:
-
α,α′-Azaisobutyronitrile
- ASE:
-
Aromatic stabilization energy;
- BETS:
-
Bis(ethylenedithio)tetraselenafulvalene;
- COD:
-
Cyclooctadiene;
- DMAD:
-
Dimethyl acetylenedicarboxylate;
- DRE:
-
Dewar resonance energy;
- GPx:
-
Glutathione peroxidase;
- HMDS:
-
Hexamethyldisilazane;
- HMPA:
-
Hexamethylphosphoric triamide;
- HOMA:
-
Harmonic oscillator model of aromaticity;
- IL:
-
Interleukine;
- IFN:
-
Interferon;
- LDA:
-
Lithium diisopropylamide;
- LHMDS:
-
Lithium hexamethyldisilazide;
- MCPBA:
-
m-Chloroperoxybenzoic acid;
- MIC:
-
Minimal inhibitory concentration;
- NICS:
-
Nucleus independent chemical shifts;
- OLED:
-
Organic light-emitting diode;
- OTFT:
-
Organic thin film transistor;
- PBL:
-
Peripheral blood leukocytes;
- PDSE:
-
Poly-1,2-bis(seleninyl)ethene;
- PEDOS:
-
Poly-3,4-ethylenedioxyselenophene;
- PEDOT:
-
Poly-3,4-ethylenedioxythiophene;
- PS:
-
Polyselenophene;
- RF-ID:
-
Radio frequency identification;
- TBHP:
-
t-Butyl hydroperoxide;
- TMEDA:
-
1,1,4,4-Tetramethylethylenediamine;
- TMSF:
-
Tetramethylselenafu-lvalene;
- TNF:
-
Tumor necrosis factor
References.
Christiaens LEE (1996) Selenophenes. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 2.13, p 731
Larsen RD (1996) 1,2-Selenazoles. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 3.07, p 475
Larsen RD (1996) 1,3-Selenazoles. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 3.08, p 493
Pedersen CTh, Becher J (1996) Two adjacent heteroatoms with at least one selenium and tellurium. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 3.13, p 659
Becher J, Pedersen CTh, Mork P (1996) Two nonadjacent heteroatoms with at least one selenium and tellurium. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 3.14, p 679
Reid DH (1996) Three or four heteroatoms including at least one selenium or tellurium. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 4.21, p 743
Christiaens LEE (1996) Six-membered rings with one selenium or tellurium atom. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 5.11, p 619
Sainsbury M (1996) Six-membered rings with two or more heteroatoms with at least one selenium or tellurium. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 6.24, p 878
Terem B (1996) Bicyclic systems with ring junction sulfur, selenium or tellurium atom. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, chap 8.32, p 833
Mƚochowski J (2008) 1,2-Selenazoles. In: Katritzky AR, Ramsden CA, Scriven EVF, Taylor RJK (eds) Comprehensive heterocyclic chemistry III. Elsevier, Oxford, chap 4.7
Devillanova FA (2006) Handbook of chalcogen chemistry: new perspectives in sulfur, selenium and tellurium. University of Cagliari, Italy
Seshadri V, Selampinar F, Sotzig GA (2004) Prog Heterocycl Chem 16:98
Janosik T, Bergman J (2005) Prog in Heterocycl Chem 17:84
Litvinov VP, Dyachenko WD (1997) Russ Chem Rev 66:923
Gronovitz S (1998) Phosphorus Sulfur Silicon Relat Elem 138:59
Mƚochowski J, Kloc K, Lisiak R, Potaczek P, Wójtowicz H (2007) ARKIVOC vi:14
Mƚochowski J, Brząszcz M, Giurg M, Palus J, Wojtowicz H (2003) Eur J Org Chem, p 4329
Mƚochowski J, Brząszcz M, Chojnacka M, Giurg M, Wójtowicz H (2004) ARKIVOC iii:226
SorianoGarcia M (2004) Curr Med Chem 11:1657
Mugesh G, Singh KB (2000) Chem Soc Rev 29:347
Mugesh G, Du Mont WW, Sies H (2001) Chem Rev 101:2125
Takimiya K, Kunugi Y, Konda Y, Ebata H, Toyoshima Y, Otsubo T (2006) J Am Chem Soc 128:3044
Jenkins IH, Salzner U, Pickup PG (1996) Chem Mater 8:2444
Rovira C (2004) Chem Rev 104:5289
Casado J, Oliva MM, Delgado MCR, Ortiz RP, Quirante JJ, Navarette J, Takimiya K, Otsubo T (2006) J Phys Chem A 110:7422
Bird CW, Cheeseman GWH (1984) Structure of five-membered rings with one heteroatom. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry. Pergamon, Oxford, chap 3.01, p 1
Nyulaszi L, Keglevich G, Quin L (1996) J Org Chem 61:7808
Balaban AT, Omiciu DC, Katritzky AR (2004) Chem Rev 104:2777
Cyrański MK (2005) Chem Rev 105:3773
Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 3839
Krygowski TM (1993) J Chem Inf Comput Sci 33:70
Krygowski TM, Cyrański MK (2001) Chem Rev 101:1385
De Proft F, Geerlings P (2001) Chem Rev 101:1451
Detty MR (1984) Five-membered rings containing one selenium or tellurium atom and one other group VI atom and their benzo derivatives. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry I. Pergamon, Oxford, chap 4.35, p 448
Schleyer PvR, Maerker C, Dronsfeld A, Jao H, Hommes HJRvE (1996) J Am Chem Soc 118:6317
Chen Z, Wannere CS, Corminbeouf, Puchta R, Schleyer PvR (2005) Chem Rev 105:3842
Bird CW (1985) Tetrahedron 41:1409
Francis MD, Hibbs DE, Hitchcock PB, Hursthouse MB, Jones C, Mackewitz T, Nixon JF, Nyulaszi L, Regitz M, Sakarya N (1999) J Organomet Chem 580:156
Nyulaszi L, Varnai P, Krill S, Regitz M (1995) J Chem Soc Perkin Trans II, p 315
Nyulaszi L (2001) Chem Rev 101:1229
Rosenbaum K, Beyer L, Richter R, Hoyer E (1992) Z Anorg Allg Chem 617:89
Wolmershauser G, Kaim W, Heckmann G, Lichtblau A (1992) Z Naturforsh B 47:675
Bernasconi CF, Zheng H (2006) J Org Chem 71:8203
Raczyńska ED, Kosińska W, Ośmiaƚowski B, Gawinecki R (2005) Chem Rev 105:3561
Zubatyuk RI, Volovenko YM, Shishkin OV, Gorb L, Leszczyński J (2006) J Org Chem 72:725
Elguero J, Katritzky AR, Dfnisko OV (2000) Adv Heterocycl Chem 76:1
Kloc K, Mƚochowski J (2001) Tetrahedron Lett 42:4899
Kloc K, Osajda M, Mƚochowski J (2001) Chem Lett 826
Dellecker F, Peisker A (1991) Chem Ztg, p 115
Mhizha S, Mƚochowski J (1997) Synth Commun 27:283
Kloc K, Maliszewska I, Mƚochowski J (2003) Synth Commun 33:3805
Zeni G (2005) Tetrahedron Lett 46:2647
Takahashi K, Tarutani S (1996) Heterocycles 43:1927
Franchetti P, Cappellacci L, Abu Sheikha G, Jayaram HN, Gurudult VV, Sint T, Schneider BP, Jones WD, Goldstein BM, Perra G, De Montis A, Loi AG, Colla PL, Grifantini M (1997) J Med Chem 40:1731
Bird CW, Cheeseman GWW, Hornfeldt AB (1984) Selenophenes, tellurophenes and their benzo derivatives. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry I. Pergamon, Oxford, chap 3.16, p 935
Maria PD, Fontana A, Siani G, Spinelli D (1998) Eur J Org Chem 1867
Lebedev MV, Nenajdenko VG, Balenkova ES (1998) Synthesis, p 89
Srikanth N, Tan CH, Ng SC, Loh TP, Koch LL, Sim KY (1997) J Chem Res (S), p 274
Jones RL, Elder MJ, Even JA (2005) Phosphorus Sulfur Silicon Relat Elem 180:827
Keil D, Hartmann H, Zug I, Schroeder A (2000) J Pract Chem 342:169
Ryu CK, Han JY, Jung OJ, Lee SK, Jung Y, Jeong SH (2005) Bioorg Med Chem Lett 15:679
Magdesieva NN (1970) Adv Heterocycl Chem 12:1
Elvidge JA, Jones JR, O'Brien C, Evans EA, Sheppard HC (1974) Adv Heterocycl Chem 16:1
Hilmey DG, Abe M, Nelen MI, Stilts CE, Baker GA, Bright FV, Davies CR, Gollnick SO, Oseroff AR, Gibson SL, Hilf R, Detty MR (2002) J Med Chem 43:2403
Stilts CE, Nelen MI, Hilmey DG, Davies SR, Gollnick SO, Oseroff AR, Gibson SL, Hilf R (2000) J Med Chem 43:2403
You Y, Gibson SL, Hilf RD, Davies SR, Oseroff AR, Roy I, Ohulchanskyy TY, Bergey EJ, Dett MR (2003) J Med Chem 46:3734
Narayanan SJ, Sridevi B, Chandrashekar TK, Vij A, Roy R (1999) J Am Chem Soc 121:9053
Seenisemy J, Bashyam S, Gokhale V, Vankayalpati HSD, Siddileni-Jain A, Steiner N, Shin-ya K, White E, Wilson WD, Hurley LH (2005) J Am Chem Soc 127:2944
Lomas JS, Lacroix JC, Vaissermann J (1999) J Chem Soc Perkin Trans II, p 2001
Srinivasan A, Pushpan SK, Ravikumar M, Chandrashekar TK, Roy R (1999) Tetrahedron 55:6671
Srinivasan A, Anand VG, Narayanan SJ, Pushpan SK, Kumar MR, Chandrashekar TK (1999) J Org Chem 64:8693
Vvedenskij VY, Shtefan ED, Mayushenko RN, Shikin EV (1997) Chem Heterocycl Compd 33:426
Takahashi K, Gunji A, Yanagi K, Miki M (1996) J Org Chem 61:4784
Pfeiffer WD (2001) Annulated Isoselenazole Compounds. In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 21, p 931
Lok R, Leone RE, Williams AJ (1996) J Org Chem 61:3286
Geisler K, Kuenzler A, Below H, Bulka E, Pfeiffer WD, Langer P (2004) Synthesis, p 97
Santos R, Fernandes LM, Boto RF, Simoes R, Almeida P (2006) Tetrahedron Lett 47:6723
Wright SW, Mc Clure LD (2004) J Heterocyclic Chem 41:1023
Robl JA, Sulsky R, Sun CQ Simpkius LM, et al. (2001) J Med Chem 44:851
Yang R, Tian R, Quiong H, YangbW, Ceo Y (2003) Macromolecules 36:743
Velusamy M, Thomas KRJ, Jiann T, Wen YS (2005) Tetrahedron Lett 46:7647
Lalezari I (1984) Five membered selenium-nitrogen heterocycles. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry I. Pergamon, Oxford, chap 4.20, p 334
Drevko BI, Smushkin MI, Kharchenko VG (1997) Chem Heterocycl Compd 33:520
Young DN, Detty MR (1997) J Org Chem 62:4692
Sashida H, Minamida H, Yamamoto K (2000) J Chem Res (S) 12:572
Sashida H, Yoshida M, Minamida H, Teranishi M (2002) J Heterocycl Chem 39:405
Sashida H, Minamida H (2004) Chem Pharm Bull 52:485
Sashida H, Ohyanagi K (1999) Heterocycles 51:17
Ohyanagi K, Sashida H (2006) Heterocycles 68:505
Nakayama J, Matsui T, Sugihara Y, Ishii A, Kumakura S (1996) Chem Lett 269
Umezawa T, Sugihara Y, Ishi A, Nakayama J (1998) J Am Chem Soc 120:12351
Mƚochowski J, Kloc K, Syper L, Inglot AD, Piasecki A (1993) Liebigs Ann Chem 1239
Wójtowicz H, Brząszcz E, Kloc K, Mƚochowski J (2001) Tetrahedron 57:9743
Nakashima Y, Shimizu T, Hirabayashi K, Kamitaga N (2005) J Org Chem 70:868
Kumka A, Chojnacka M, Kloc K, Palus J, Mossakowska I, Wójcik G, Mƚochowski J (2005) Ann Pol Chem Soc, p 104
Chojnacka M (2007) PhD thesis, Wrocƚaw University of Technology
Lisiak R, Mƚochowski J, Palus J (2007) Polish J Chem 81:1403
Winkler JD, Finc-Estes M (1989) Tetrahedron Lett 30:7293
Umemoto T, Ishihara S (1993) J Am Chem Soc 115:2156
Bird CW, Cheeseman GWH (1984) Reactivity of five-membered rings with one heteroatom. In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry I. Pergamon, Oxford, chap 3.02, p 40
Pardel A, Ramos SS, Santos PF, Reis LV, Almeida P (2002) Molecules 7:320
Vassilev A, Dikova I, Deligeorgiev T, Drexhage KH (2004) Synth Commun 34:2539
Lalezari I, Shafiee A, Yalpani M (1979) Adv Heterocycl Chem 24:109
Butler RN, Fox A (2001) J Chem Soc Perkin Trans I, p 394
Hong SY, Jun H, Yoon SS, Kang C, Such M (2004) Chem Lett 33:318
Quast H, Ivanova S, Peters EM, Peters K, Schnering HG (1996) Liebigs Ann Chem, p 1541
Mbui M, Christiaens LE, Renson M (1989) Bull Soc Chim Belg 98:395
Dellecker F, Peisker A (1991) Chem Ztg, p 135
Mhizha S, Mƚochowski J (1997) Synth Commun 27:283
Takikawa Y, Hikage S, Matsucha Y, Higashuayama K, Takeyshi Y, Shimada K (1991) Chem Lett, p 2043
Takimyya K, Kataoka Y, Niihara N, Aso Y, Otsubo T (2003) J Org Chem 68:5217
Zmitrovich NI, Petrov ML (1996) Zh Org Khim (Russ) 32:1870
Regitz M, Krill S (1996) Phosphorus Sulfur Silicon Relat Elem 115:99
Nishiyama Y, Hada Y, Anjiki M, Hanita S, Sonoda N (1999) Tetrahedron Lett 40:6293
Nishiyama Y, Hada Y, Anjiki M, Miyake K, Hanita S, Sonoda N (2002) J Org Chem 67:1520
Sashida H, Ohyanagi K (2005) Chem Pharm Bull 53:60
Shatz J (2000) Selenophenes. In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 11.9, p 423
Murphy J (2000) Benzo[b]selenophenes. In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 10.7, p 265
Murphy J (2000) Benzo[c]selenophenes. In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 10.8, p 305
Murphy J (2000) Dibenzoselenophenes In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 10.9, p 323
Potapov WA, Gusarova NK, Amosova CV, Kashik AC, Trofimov BA (1986) Zh Org Khim (Russ) 22:276
Deryagina EN, Sukhomazova EN, Levanova EP, Shilkina TA, Korhevin NA (2000) Zh Org Khim 36:380
Deriagina EN, Sukhomazova EN, Levanova EP, Korchevin NA, Danilova AP (2004) Zh Org Khim 40:318
Nakayama J, Mizumura A, Akiyama J, Nishio T, Jida J (1994) Chem Lett, p 77
Aloes D, Luchese C, Nagueira CW, Zeni G (2007) J Org Chem 72:6726
Dabdoub MJ, Dabdoub VB, Pereira MA, Zukerman-Schpector J (1996) J Org Chem 61:9503
Nguyen TC, Guzei IA, Lee D (2002) J Org Chem 67:6553
Aquad E, Laksmikantham MV, Cava MP (2001) Org Lett 3:4283
Arsenyan P Prediger P, Moro AV, Noguiera CW, Savegnano L, Menezes PH, Roha JBT, Zeni G (2006) J Org Chem 71:3786
Prediger P, Moro AV, Noguiera CW, Savegnono L, Menezes PH, Roha JBT, Zeni G (2006) J Org Chem 71:3786
Deryagina EN, Korchevin NA (1997) Zh Obshch Khim 67:1582
Deryagina EN, Korchevin NA, Shilkina TA, Sukhomazova EN, Levanova EP (1998) Russ Chem Bull 47:447
Holmes H, Verkruisse N, Brandsma L (1981) Chem Commun, p 336
Brandsma L, Hommes H, Verkruijsse HD de Jong RPL(1985) Rec Trav Chim Pays-Bas 104:226
Sashida H, Sadamori K, Tsuchiya T (1998) Synth Commun 28:713
Sashida H, Yasuike S (1998) J Heterocycl Chem 35:725
Zborowski YL, Levon VF, Staninetz VI (1996) Zh Obsh Khim 66:1847
Zborowski YL, Levon VF, Staninetz VI (1998) Zh Obsh Khim 68:288
Lendel VG, Pak VI, Petrus VV, Kiyak MY, Migalina YV (1999) Khim Geterotsikl Soed, p 1331
Sommen G, Comel A, Kirsh G (2005) Phosphorus Sulfur Silicon Relat Elem 180:939
Kesharwani T, Vorlikar SA, Larock RC (2006) J Org Chem 71:2307
Flynn BL, Bui CT (2006) J Comb Chem 8:163
Uemoto T, Ishihara S (1990) Tetrahedron Lett 31:3579
Engman L, Eriksson P (1996) Heterocycles 43:461
Behreus J, Hinrichs W, Link T, Schiffling C, Klar G (1995) Phosphorus Sulfur Silicon Relat Elem 101:235
Soris L, Cava M (1976) J Am Chem Soc 98:867
Amaresh RR, Laksmikantham MV, Baldwin JW, Cava MP, Metzger RM, Rogers RD (2002) J Org Chem 67:2453
Mohanakrishnan AK, Amaladess P (2005) Tetrahedron Lett 46:7201
Aquad E, Laksmikantham MV, Broker GA, Rogers RD (2003) Org Lett 5:2519
Pfeiffer WD (2001) Isoselenazoles. In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 20, p 921
Martins MAP, Bastos GP, Sinhorin AP, Zinmermann NEK, Bonacorso HG, Zanatta N (2002) Synthesis, p 2220
Lesser R, Weiss R (1924) Ber Deutsch Chem Gess 57:1077
Mƚochowski J, Gryglewski RJ, Inglot AD, Jakubowski A, Juchniewicz L, Kloc K (1996) Liebigs Ann, p 1751
Palus J, Mƚochowski J, Juchniewicz L (1998) Polish J Chem 72:1931
Osajda M, Mƚochowski J (2002) Tetrahedron 58:7531
Osajda M, Kloc K, Mƚochowski J, Piasecki E, Rybka K (2001) Polish J Chem 75:823
Nakashima Y, Shimizu T, Hirabayashi K, Komitaga (2005) J Org Chem 70:868
Cantineau R, Tihang G, Plenevaux A, Christiaens LE, Guillaume M, Welter A, Dereu N (1986) J Labelled Compd Radiopharm 23:59
Gadanyi S, Kalai T, Jeko J, Berente Z, Hideg K (2000) Synthesis, p 2039
Kalai T, Mugesh G, Roy G, Sies H, Berente Z, Hideg K (2005) Org Biomol Chem 3:3564
Osajda M, Mƚochowski J (2003) Synth Commun 33:1301
Liu Y, Li B, Li L, Hang HY (2002) Helv Chim Acta 85:9
Hu L, Lu S, Yang F, Feng J, Liu Z, Hu H, He H (2002) Phosphorus Sulfur Silicon Relat Elem 177:2785
Zhou J, Chen R (1999) Heteroatom Chem 10:247
Wójtowicz-Mƚochowska H, Soroko G, Mƚochowski J (2008) Synth Commun 38 (in press)
Xue Z, Hou AX, Kwong DWJ, Wong WK (2007) Bioorg Med. Chem Lett 17:4266
Engman L, Hallberg A (1989) J Org Chem 54:2964
Oppenheimer J, Silks LA (1996) J Labelled Compd Radiopharm 28:281
Kersting B, DeLion M (1999) Z Naturforsch B 54:1042
Chang TH, Huang ML, Hsu WL, Hwang JM, Hsu LY (2003) Chem Pharm Bull 51:1413
Filipovska A, Kelso GF, Brown SE, Beer SM, Smith RAJ, Murphy MP (2005) J Biol Chem 280:24113
Zade SS, Panda S, Singh HB, Wolmeshauser (2005) Tetrahedron Lett 46:665
Fong MC, Shiesser CH (1997) J Org Chem 62:3103
Pfeiffer WD (2001) Selenazoles. In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 11.22, p 941
Pfeiffer WD (2001) Annulated selenazole compounds. In: Houben–Weil science of synthesis, Thieme, Stuttgart, chap 11.23, p 991
Below H, Pfeiffer WD, Geisler K, Lalk M, Langer P (2005) Eur J Org Chem, p 3637
Moriarty RM, Vaid BK, Duncan MP, Levy SG, Prakash O, Goyal S (1992) Synthesis, p 845
Zhang PF, Chen ZC (2000) Synthesis, p 1219
Purseigle E, Dubreuil D, Marchaud A, Pradere JP, Goli M, Toupet L (1998) Tetrahedron 54:2545
Hartmann H, Eckert K, Schroder A (2000) Angew Chem Int Ed Engl 39:536
Maeda H, Kambe H, Sonoda N (1997) Tetrahedron 53:13667
Brovarets VS, Drach BS (1986) Zh Obshch Khim 56:321
Brovaretz VS, Vydzhak RN, Vinogradova TK, Drach BS (1993) Zh Obshch Khim 63:87
Brovaretz VS, Zyus KV, Romanenko EA, Drach BS (1995) Zh Obshch Khim 65:1972
Bryce MR, Fakley ME (1988) Synth Commun 18:181
Couture A, Grandclaudon P, Huguerre E (1987) Synthesis, p 363
Fujiwara S, Asanuma Y, Shin-ike T, Kambe N (2007) J Org Chem 72:8087
Lalezari I, Schafiee A, Yalpani M (1970) Angew Chem Int Ed Engl 82:484
Jackson YA, White CL, Lakshmikantham MV, Cava MP (1987) Tetrahedron Lett 28:5635
Moavad EB, Yousif MY, Metwally MA (1989) Pharmazie 44:820
Zmitrovich NI, Petrov ML (1996) Zh Org Khim 32:1870
Shimada K, Matsuda Y, Hikage S, Takeishi Y, Takikawa Y (1991) Bull Chem Soc Jpn 64:1037
Al-Rubaie AZ, Yousif LZ, Al-Homad AJH (2002) J Organometal Chem 656:274
Huang X, Chen J (2003) Synth Commun 33:2823
Shaffiee A, Ebrahimzadeh MA, Malehi A (1999) J Heterocyclic Chem 36:901
Sharma KS, Sumar LSG (1984) Indian J Chem 23B:180
Sharma KS, Kumar GV, Kumari S (1986) Indian J Chem 25B:500
Sergheev WA, Pesin WG, Papirnik LR (1989) Zh Org Khim 25:1802
Praefcke K, Kohne WG, Korinth F (1990) Liebigs Ann Chem, p 203
Lash TD, Colby DA, Graham SR, Chaney ST (2004) J Org Chem 69:8851
Sessler JL, Gebauer A, Vogel E (2000) In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 2. Academic, San Diego, p 1
Lash TD (2000) In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 2. Academic, San Diego, p 125
Latos-Grażyński L (2000) In: Kadish KM, Smith KM, Guilard R (eds) The porphyrin handbook, vol 2. Academic, San Diego, p 361
Chandrashekar TK, Venkatramar S (2003) Acc Chem Res 36:676
Chandrashekar TK, Venkatramar S, Prabhuraja V, Misra R, Basker V (2005) Phosphorus Sulfur Silicon Relat Elem 180:845
Hilmey DG, Abe DM, Nelen MI, Stilts CE, Baker GA, Baker SN, Bright FV, Davies SR, Gollnick SO, Oseroff AR, Gibson SL, Hilf R, Detty MR (2002) J Med Chem 45:449
Rath H, Sankar J, PrabhuRaja V, Chandrashekar TK, Nag A, Goswami D (2005) J Am Chem Soc 127:11608
Misra R, Kumar R, Chandrashekar TK, Joshi BS (2006) J Org Chem 72:1153
Anand VG, Pushpan SK, Venkatraman S, Deepa S, Sastry GN (2002) J Org Chem 67:6309
Latos-Grażyński L, Pacholska E, Szternberg L, Ciunik Z (2000) J Org Chem 65:8188
Latos-Grażyński L, Pacholska E, Chmielewski PJ, Olmstead MM, Balch AL (1996) Inorg Chem 35:566
Stilts CE, Nelen MI, Hilmey DG, Davies SR, Gollnick SO, Oseroff AR, Gibson SL, Hild R, Detty MR (2000) J Med. Chem 43:2403
Bruckner C, Sternberg ED, Boyle RW, Dolphin D (1997) Chem Commun, p 1689
Narayanan SJ, Sridevi B, Chandrashekar TK, Vij A, Roy R (1999) J Am Chem Soc 121:9053
Doddi E, Ercolani G (1994) Adv Heterocycl Chem 60:65
Murphy PJ (2003) Selenopyrylium and benzoselenopyrylium salts In: Houben–Weil science of synthesis. Thieme, Stuttgart, chap 14.10, p 817
Sashida H, Ohyanagi K (1999) Heterocycles 51:17
Sashida H, Ohyanagi K, Minoura M, Akiba K (2002) J Chem Soc Perkin I, p 606
Sashida H, Yashida M, Minamida H, Teraniski M (2002) J Heterocycl Chem 32:405
Sashida H, Ohyanagi K (2004) Chem Pharm Bull 52:57
Sashida H, Ohynagi K (2005) Chem Pharm Bull 53:60
Drevko BI, Fomenko LA, Suchkov MA, Kharchenko VG (1999) Khim Geterotsikl Soedin 35:749
Abaev VT, Dzaraeva LB, Blinkhvatov AF, Okhlobystin OY (1998) Zh Obshch Khim 68:768
Detty MR, Young DN, Williams AJ (1995) J Org Chem 60:6631
Simard TP, Yu JH, Zebrowski-Young JM, Haley NF, Detty MR (2000) J Org Chem 65:2236
Leonard KA, Nelen MI, Anderson LT, Gibson SL, Hilf R, Detty MR (1999) J Med Chem 42:3942
Leonard KA, Nelen MI, Simard TP, Davies SR, Gollanick SO, Oseroff AR, Gibson SL, Hilf R, Chen LB, Detty MR (1999) J Med Chem 42:3953
Leonard KA, Hall JP, Nelen MI, Davies SR, Gollnick SO, Comacho S, Oseroff AR, Gibson SL, Hilf R, Detty MR (2000) J Med Chem 43:4488
Detty MR, Gibson SL, Hilf R (2004) Bioorg Med Chem 12:2589
Lalezari I, Schaffie A, Yalpani M (1970) Angew Chem Int Ed Engl 9:464
Gleiter A, Kratz D, Schafer W, Schelmann K (1991) J Am Chem Soc 113:9258
Detert H, Anthony-Maeyer C, Meier H (1992) Angew Chem Int Ed Engl 31:791
Grivas S (2000) Current Org Chem 4:707
Grivas S, Tian W (1992) Acta Chem Scand 46:1109
Tian W, Grivas S (1992) J Heterocycl Chem 29:1305
Tian W, Grivas S (1992) Synthesis, p 1283
Tian W, Grivas S, Olsson K (1993) J Chem Soc Perkin Trans I, p 257
Grivas S, Tian W, Lindstrom S, Ronne E, Olsson K (1993) Acta Chem Scand 47:521
Mƚochowski J, Giurg M, Kubicz E, Said SB (1996) Synth Commun 26:291
Giurg M, Wójtowicz H, Mƚochowski J (2002) Polish J Chem 76:537
Said SB, Skarżewski J, Mƚochowski J (1989) Synthesis, p 223
Brząszcz M, Kloc K, Mƚochowski J (2003) Polish J Chem 77:1579
Wójtowicz H, Mƚochowski J (2001) Ann of the Polish Chem Soc, p 74
Wójtowicz H, Mƚochowski J, Syper L, Yadav HS (2006) Synth Commun 36:1991
Giurg M, Wiech E, Piekielska K, Gębala M, Mƚochowski J, Wolański M, Ditkowski B, Peczyńska-Czoch W (2006) Polish J Chem 80:297
Brząszcz M (2004) PhD thesis, Wrocƚaw University of Technology
Carland M, Fenner T (2005) The use of selenium-based drugs in medicine, In: Gielen M, Tieking ERT (eds) Metallotherapeutic drugs and metal-based diagnostic agents. Wiley, Chichester, chap 17, p 313
Nakamura Y, Feng Q, Kumagai T, Torikai K, Ohigashi H, Osawa T, Noguchi N, Niki E, Uchida K (2002) J Biol Chem 277:2687
Yoshizumi M, Kogame T, Suzaki Y, Fujita Y, Kyaw M, Kirima K, Ishizawa K, Tsuchiya K, Kagami S, Tamaki T (2002) British J Pharm 136:1023
Zhao R, Holmgren A (2002) J Biol Chem 277:39456
Back TG, Dyck BP (1997) J Am Chem Soc 119:2079
Jaquemin PV, Christiaens LE, Renson MJ, Evers MJ, Dereu N (1992) Tetrahedron Lett 33:3863
Erdelmeier I, Tailhal-Lomont C, Yadan SC (2000) J Org Chem 65:8152
Reich HJ, Jasperse CP (1987) J Am Chem Soc 109:5549
Ostrovidov S, Franck P, Joseph D, Martarello L, Kirsh G, Belleville F, Nabet P, Dousset BJ (2000) J Med Chem 43:1762
Back TG, Kuzma D, Parvez M (2005) J Org Chem 70:9230
Yang X, Wang Q, Xu H (2002) Carbohydrate Res 337:1309
Sun Y, Mu Y, Ma S, Gong P, Yan G, Liu J, Shen J, Luo G (2005) Biochim Biophys Acta 1743:199
Wang SF, Komarov P, Sies H, de Groot (1992) Hepatology 15:1112
Hatchett RJ, Gryglewski RJ, Mƚochowski J, Zembowicz A, Radziszewski W (1994) J Physiol Pharmacol 45:55
Southan GJ, Salman AL, Shabo C (1996) Life Sci 58:1139
Franchetti P, Cappellacci L, Grifantini M, Barzi A, Nocentini G, Yang H, O'Connor A, Jayaram HN, Carrell C, Goldstein BM (1995) 38:3829
Franchetti P, Cappellacci L, Abu Sheikha G, Jayaram HN, Gurudutt VV, Sint T, Schneider BP, Jones WD, Goldstein BM, Perra G, De Montis A, Loi AG, La Colla P, Grifantini M (1997) J Med Chem 40:1731
Franchetti P, Cappellaci L, Perlini P, Jayaram HN, Butter A, Schneider BP, Collart FR, Huberman E, Grifantini M (1998) J Med Chem 41:1702
Schewe C, Schewe T, Wendel A (1994) Biochem Pharmacol 48:65
Ito H, Wang JZ, Shimura K, Sakahibara J, Ueda T (1990) Anticancer Res 10:891
Kumar Y, Green R, Borysko KZ, Wise DS, Wotring LL, Townsed LB (1993) J Med Chem 36:3843
Kumar Y, Green R, Wise DS, Worting LL, Townsed LB (1993) J Med Chem 36:3849
Koketsu M, Ishihara H, Wu W, Murakami K, Saiki I (1999) Eur J Pharm Sci 9:157
Chu CK, Ma L, Olgen S, Pierra C, Du J, Gumina G, Gullen E, Cheng YC, Shinazi RF (2000) J Med Chem 43:3906
Wójtowicz H, Kloc K, Maliszewska I, Mƚochowski J, Piętka M, Piasecki E (2004) Il Farmaco 59:863
Bień M, Bƚaszczyk B, Kalinowska K, Mƚochowski J, Ingot AD (1999) Arch Immun Ther Exp 47:185
Inglot AD, Mƚochowski J, Zielińska-Jenczylik J, Piasecki E, Ledwoń TK, Kloc K (1996) Arch Immun Ther Exp 44:67
Inglot AD, Piasecki E, Zaczyński E, Zielińska-Jenczylik J (1992) Arch Immun Ther Exp 40:169
Bƚaszczyk B, Inglot AD, Toivanen P, Mƚochowski J, Szymaniec S (1995) Arch Immun Ther Exp 43:299
Bƚaszczyk B, Inglot AD, Kowalczyk-Bronisz H, Szymaniec S, Mƚochowski J (1995) Arch Immun Ther Exp 43:305
Murphy AR, Frechet JMJ (2007) Chem Rev 107:1066
Ng SC, Chan HSO, Ong TT, Kumura K, Mazaki Y, Kabayashi K (1998) Macromolecules 31:1221
Marikami A, Takimiya K, Aso Y, Otsubo T (1999) Org Lett 1:23
Takimiya K, Oharuda A, Morikami A, Aso Y, Otsubo T (1998) Angew Chem Int Ed Engl 37:619
Takimiya K, Kataoka Y, Niihara N, Aso Y, Otsubo TJ (2003) J Org Chem 68:5217
Friend RH (2001) Pure Appl Chem 73:425
Montheard JP, Pascal T, Seytre G, Staffan-Boitex G, Douillard A (1984) Synth Met 9:389
Sugimoto R, Yoshino K, Inoue S, Tsukagoshi K (1985) Jpn J Appl Phys Part 2 24:425; Chem Abstr (1985) 103:88274
Sugimoto R, Takeda J, Asanuma T (1987) Jpn Kokai 62106923; Chem Abstr (1987) 107:199187
Matsushita Elec, Ind, Co Ltd (1984) Jpn Kokai 59191727; Chem Abstr (1985) 102:114170
Shinko Kagaku Kogyo KK (1985) Jpn Kokai 6050194; Chem Abstr (1985) 103:78307
Glenis S, Ginley DS, Frank AJ (1987) J Appl Phys 62:190
Peulon V, Barbey G, Outurquin F, Paulmier C (1993) Synth Met 53:115
Iwatsuki S, Kubo M, Kamei N (1992) Chem Lett, p 1551
Yang R, Tian R, Yan J, Hang Y, Yang, Hou Q, Yang W, Zhang C, Cao Y (2005) Macromolecules 38:244
Kirchmeyer S, Reuter K, Simpson JC (2007) Poly(3,4-ethylenedioxythiophene) – scientific importance, remarkable properties, and applications. In: Skotheim TA, Reynolds JR (eds) Handbook of conducting polymers. CRC, Boca Raton, chap 10, p 1
Bendikov M (2007) In: Abstracts of 10th international conference on the chemistry of selenium and tellurium, Łódz, Poland, June 2007. Łódz University Press, abstract SL33
Patra A, Zade SS, Wijsboom YH, Bendikov M (2007) In: Abstracts of the 72nd meeting of the Israel Chemical Society, Tel-Aviv, 6–7 Feb 2007. Available at: http://www.weizmann.ac.il/usersfiles/ics2007/2007/abstracts/485.html.Last accessed 2May 2008
Wijsboom YH, Patra A, Zade A, Zade SS, Bendikov M (2007) In: Abstracts of the 72nd meeting of the Israel Chemical Society, Tel-Aviv, 6–7 Feb 2007. Available at: http://www.weizmann.ac.il/usersfiles/ics2007/2007/abstracts/492.html.Last accessed 2May 2008
Kunugi Y, Takimiya K, Yamane K, Yamashita K, Aso Y, Otsubo T (2003) Chem Mater 15:6
Casado J, Oliva MM, Delgado MCR, Ortiz RP, Quirante JJ, Navarette JTL, Takimiya K, Otsubo T (2006) J Phys Chem A 110:7422
Feeder N, Less RJ, Rawson JM, Oliette P, Palacio F (2000) Chem Commun, p 2449
Beer L, Brusso JL, Cordes AV, Haddon RC, Itkis ME, Kirschbaum K, MacGregor DG, Oakley RT, Pinkerton AA, Reed RW (2002) J Am Chem Soc 124:9498
Beer L, Brusso JL, Haddon RC, Itkis ME, Oakley RT, Reed RW, Richardson JF, Secco RA, Yu X (2005) Chem Commun, p 5745
Beer L, Brusso JL, Haddon RC, Itkis ME, Kleinke H, Leitch AA, Oakley RT, Reed RW, Richardson JF, Secco RA, Yu X (2005) J Am Chem Soc 127:18159
Beer L, Brusso JL, Haddon RC, Itkis ME, Leith AA, Oakley RT, Reed RW, Richardson JF (2005) Chem Commun, p 1543
Brusso JL, Cvrkalj K, Leith AA, Oakley RT, Reed W, Robertson CM (2006) J Am Chem Soc 128:15080
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Młochowski, J., Giurg, M. (2008). New Trends in Chemistry and Application of Aromatic and Related Selenaheterocycles. In: Topics in Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_7
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