Abstract
The benzotriazole fragment is known to behave as (1) an excellent leaving group, (2) an electron-donating or an electron-withdrawing group, (3) an anion precursor, and (4) a radical precursor. It confers unique physicochemical properties to its immediate vicinity on various molecular scaffolds. This review covers the preparation and synthetic utility of versatile benzotriazole derivatives. The selected compounds are conveniently prepared from 1H-benzotriazole and are characterized by a huge synthetic potential. Their specific reactivity is discussed and illustrated with various examples ranging from methodology in organic chemistry to the total synthesis of complex structures.
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Panda SS, Hall CD, Scriven E, Katritzky AR (2013) Aldrichimica Acta 46:43
Monbaliu JCM, Katritzky AR (2012) Chem Commun 48:11601
Katritzky AR, Rachwal S (2011) Chem Rev 111:7063
Katritzky AR, Rachwal S (2010) Chem Rev 110:1564
Katritzky AR, Manju K, Singh SK, Meher NK (2005) Tetrahedron 61:2555
Katritzky AR, Rogovoy BV (2003) Chem Eur J 9:4586
Katritzky AR, Lan X, Yang JZ, Denisko OV (1998) Chem Rev 98:409
Katritzky AR, Belyakov SA (1998) Aldrichimica Acta 31:35
Katritzky AR, Wu H, Xie L, Rachwal S, Rachwal B, Jiang J, Zhang G, Lang H (1995) Synthesis 1315
Katritzky AR, Rachwal S, Hitchings GJ (1991) Tetrahedron 47:2683
El-Faham A, Albericio F (2011) Chem Rev 111:6557
Joullié MM, Lassen KM (2010) ARKIVOC 8:189
Valeur E, Bradley M (2009) Chem Soc Rev 38:606
Rees CW, Storr RC (1969) J Chem Soc C 1474
Monbaliu JCM, Beagle LK, Kovacs J, Zeller M, Stevens CV, Katritzky AR (2012) RSC Adv 2:8941
Sasse MJ, Storr RC (1978) J Chem Soc Perkin Trans 1 909
Mandal B, Basu B (2014) RSC Adv 4:13854
Panmand DS, Tiwari AD, Panda SS, Monbaliu JCM, Beagle LK, Asiri AM, Stevens CV, Steel PJ, Hall CD, Katritzky AR (2014) Tetrahedron Lett 55:5898
Kumar D, Mishra BB, Tiwari VK (2014) J Org Chem 79:251
Fraix A, Le Gall T, Berchel M, Denis C, Lehn P, Montier T, Jaffrès PA (2013) Org Biomol Chem 11:1650
Gnamm C, Jeanguenat A, Dutton AC, Grimm C, Kloer DP, Crossthwaite AJ (2012) Bioorg Med Chem Lett 22:3800
Reddie KG, Humphries WH, Bain CP, Payne CK, Kemp ML, Murthy N (2012) Org Lett 14:680
Hunter R, Msutu A, Dwyer CL, Emslie ND, Hunt RC, Bezuidenhoudt BCB (2011) Synlett 2011:2335
Stellenboom N, Hunter R, Caira MR (2010) Tetrahedron 66:3228
Stellenboom N, Hunter R, Caira MR, Szilágyi L (2010) Tetrahedron Lett 51:5309
Pietrzak M, Wehling JP, Kong S, Tolstoy PM, Shenderovich IG, López C, Claramunt RM, Elguero J, Denisov GS, Limbach H-H (2010) Chem Eur J 16:1679
Teague SJ, Barber S (2010) Tetrahedron Lett 51:4720
Katritzky AR, Widyan K, Gyanda K (2008) Synthesis 1201
Katritzky AR, Vincek AS, Steel PJ (2008) Heterocycles 76:1401
Hunter R, Caira M, Stellenboom N (2006) J Org Chem 71:8268
Katritzky AR, Witek RM, Rodriguez-Garcia V, Mohapatra PP, Rogers JW, Cusido J, Abdel-Fattah AAA, Steel PJ (2005) J Org Chem 70:7866
Katritzky AR, Abdel-Fattah AAA, Vakulenko AV, Tao H (2005) J Org Chem 70:9191
Katritzky AR, Hayden AE, Kirichenko K, Pelphrey P, Ji Y (2004) J Org Chem 69:5108
Katritzky AR, Rodriguez-Garcia V, Nair SK (2003) J Org Chem 69:1849
Gibson CL, La Rosa S, Suckling CJ (2003) Org Biomol Chem 1:1909
Greci L, Castagna R, Carloni P, Stipa P, Rizzoli C, Righi L, Sgarabotto P (2003) Org Biomol Chem 1:3768
Ponce MA, Tarzi OI, Erra-Balsells R (2003) J Heterocycl Chem 40:419
Katritzky AR, Vakulenko AV, Jain R (2003) Arkivoc 2003:131
Katritzky AR, Rogovoy B, Klein C, Insuasty H, Vvedensky V, Insuasty B (2001) J Org Chem 66:2854
Katritzky AR, Nichols DA, Voronkov MV (2000) Arkivoc 2000:667
Katritzky AR, Voronkov MV, Pastor A, Tatham D (1999) Heterocycles 51:1877
Hughes TV, Hammond SD, Cava MP (1998) J Org Chem 63:401
Bonesi SM, Erra-Balsells R (1997) J Heterocycl Chem 34:891
Katritzky AR, Ignatchenko AV, Lan X, Lang H, Stevens CV (1994) Tetrahedron 50:6005
Katritzky AR, Ignatchenko AV, Lang H (1995) Heterocycles 41:131
Katritzky AR, Belyakov SA, Lam JN, Dupont Durst H, Karpenko DV (1994) Heterocycles 39:73
Toth JE, Ray J, Deeter J (1993) J Org Chem 58:3469
Fujihara H, Oi N, Erata T, Furukawa N (1990) Tetrahedron Lett 31:1019
Barker SJ, Storr RC (1990) J Chem Soc Perkin Trans 1 3:485
Kim JN, Ryu EK (1990) Synth Commun 20:1373
De Rosa M, Quesada PA, Dodsworth DJ (1987) J Org Chem 52:173
Ganapathy K, Gurumurthy R, Mohan N, Sivagnanam G (1987) Monatsh Chem 118:583
Wender PA, Cooper CB (1986) Tetrahedron 42:2985
Berti C, Greci L, Andruzzi R, Trazza A (1986) J Chem Soc Perkin Trans 1 4:607
Pyne SG (1986) J Org Chem 51:81
Akasaka T, Furukawa N, Oae S (1985) Phosphorus Sulfur 21:277
Berti C, Greci L, Andruzzi R, Trazza A (1982) J Org Chem 25:4895
Keating M, Sasse MJ, Storr RC (1978) J Chem Soc Perkin Trans 1 905
Lichman KV (1971) J Chem Soc C 2539
Rees CW, Storr RC (1969) J Chem Soc C 1478
Niedermann K, Früh N, Senn R, Czarniecki B, Verel R, Togni A (2012) Angew Chem Int Ed 51:6511
Katritzky AR, Shobana N, Juliusz P, Afridi AS, Fan WQ (1992) Tetrahedron 48:7817
Taboada R, Ordonio GG, Ndakala AJ, Howell AR, Rablen PR (2003) J Org Chem 68:1480
Boto A, Hernández D, Hernández R (2010) Eur J Org Chem 2010:6633
Lesiv AV, Ioffe SL, Strelenko YA, Tartakovsky VA (2002) Helv Chim Acta 85:3489
Birkofer L, Richter P, Ritter A (1960) Chem Ber 93:2804
Sureshbabu VV, Chennakrishnareddy G, Hemantha HP (2010) Synlett 2010:715
Katritzky AR, Khashab NM, Gromova AV (2006) Arkivoc 2006:226
Katritzky AR, Ledoux S, Witek RM, Nair SK (2004) J Org Chem 69:2976
Larsen C, Steliou K, Harpp DN (1978) J Org Chem 43:337
Boto A, Hernández D, Hernández R, Álvarez E (2007) J Org Chem 72:9523
Katritzky AR, Donkor A, Fang Y (2001) J Org Chem 66:4041
Katritzky AR, Stevens CV, Zhang GF, Jiang J (1995) Heterocycles 40:231
Katritzky AR, Cheng D, Leeming P, Ghiviriga I, Hartshorn CM, Steel PJ (1996) J Heterocycl Chem 33:1935
Bourry A, Pitard F, Rigo B, Sanz G, Camus F, Norberg B, Durant F, Couturier D (2002) J Heterocycl Chem 39:109
Katritzky AR, Soloducho J, Musgrave RP, Breytenbach JC (1995) Tetrahedron Lett 36:5491
Katritzky AR, Hong Q, Yang Z (1995) J Org Chem 60:3405
Katritzky AR, Hong Q, Yang Z (1994) J Org Chem 59:7947
Gasparini JP, Gassend R, Maire JC (1981) J Organochem Chem 208:309
Gasparini JP, Gassend R, Maire JC (1980) J Organomet Chem 188:141
Boto A, Hernández D, Hernández R (2010) Eur J Org Chem 2010:3847
Denmark SE, Collins WR (2007) Org Lett 9:3801
Niedenzu K, Woodrun KR (1989) Inorg Chem 28:4022
Campbell CD, Rees CW (1969) J Chem Soc C 752
Knight DW, Little PB (2000) J Chem Soc Perkin Trans 1 15:2343
Tadross PM, Stoltz BM (2012) Chem Rev 112:3550
Wenk HH, Winkler M, Sander W (2003) Angew Chem Int Ed 42:502
Pellissier H, Santelli M (2003) Tetrahedron 59:701
Sanji T, Mori T, Sakurai H (2006) J Organomet Chem 691:1169
Mochida K, Kayamori T, Wakasa M, Hayashi H, Egorov MP (2000) Organometallics 19:3379
Birkett MA, Knight DW, Little PB, Mitchell MB (2000) Tetrahedron 56:1013
Harsanyi MC, Lay PA, Norris RK, Witting PK (1996) Aust J Chem 49:581
Whitney SE, Winters M, Rickborn B (1990) J Org Chem 55:929
Rigby JH, Holsworth DD, James K (1989) J Org Chem 54:4019
Del Mazza D, Reinecke MG (1988) J Org Chem 53:5799
Rickborn B, Whitney SE (1988) J Org Chem 53:5595
Cresp TM, Wege D (1986) Tetrahedron 42:6713
Ando W, Tsumuraya T (1986) Tetrahedron Asymmetry 27:3251
Anthony IJ, Wege D (1984) Aust J Chem 37:1283
Houghton PG, Rees CW (1980) J Chem Res Synop 303
Fan J, Brown SM, Tu Z, Kharasch ED (2011) Bioconjug Chem 22:752
Furusawa M, Hashimoto T, Noma Y, Asakawa Y (2006) Chem Pharm Bull 54:861
Callot HJ, Cromer R, Louati A, Gross M (1986) J Chem Soc Chem Commun 767
Perona A, Sanz D, Claramunt RM, Elguero J (2006) Molecules 11:453
El Kaim L, Meyer C (1996) J Org Chem 61:1556
Mester B, Claramunt RM, Elguero J, Atienza J, Barrio AG, Escario JA (1991) Chem Pharm Bull 39:1990
Johns AM, Liu Z, Hartwig JF (2007) Angew Chem Int Ed 46:7259
Denton JR (2010) Synthesis 775
Katritzky AR, Moutou JL, Yang Z (1995) Synlett 99
Cid BM, Lopez-Cantarero J, Duce S, Garcia Ruano JL (2009) J Org Chem 74:431
Katritzky AR, Hanci S, Meher NK (2009) Arkivoc 2009:115–124
Katritzky AR, Khelashvili L, Le KNB, Mohapatra PP, Steel PJ (2007) J Org Chem 72:5805
Katritzky AR, Monteux DA, Tymoshenko DO (1999) Org Lett 1:577
Katritzky AR, He HY, Suzuki K (2000) J Org Chem 65:8210
Micó XA, Ziegler T, Subramanian LR (2004) Angew Chem Int Ed 43:1400
Katritzky AR, El Khatib M, Bol’shakov O, Khelashvili L, Steel PJ (2010) J Org Chem 75:6532
Sitnikov NS, Kokisheva AS, Fukin GK, Neudörfl JM, Sutorius H, Prokop A, Fokin VV, Schmalz HG, Fedorov AY (2014) Eur J Org Chem 2014:6481
Roman BI, Monbaliu JCM, De Coen LM, Verhasselt S, Schuddinck B, Van Hoeylandt E, Stevens CV (2014) Eur J Org Chem 2014:2594
Lebedyeva IO, Biswas S, Goncalves K, Sileno SM, Jackson AR, Patel K, Steel PJ, Katritzky AR (2014) Chem Eur J 20:11695
Panda SS, Ibrahim MA, Küçükbay H, Meyers MJ, Sverdrup FM, El-Feky SA, Katritzky AR (2013) Chem Biol Drug Des 82:361
Baglan M, Atılgan S (2013) Chem Commun 49:5325
Frederich JH, Harran PG (2013) J Am Chem Soc 135:3788
El Khatib M, Elagawany M, Çalışkan E, Davis EF, Faidallah HM, El-Feky SA, Katritzky AR (2013) Chem Commun 49:2631
Bajaj K, Panda SS, Ibrahim MA, El-Feky SA, Katritzky AR (2013) J Pept Sci 19:110
Panda SS, Bajaj K, Meyers MJ, Sverdrup FM, Katritzky AR (2012) Org Biomol Chem 10:8985
El-Nachef C, Bajaj K, Koblick J, Katritzky AR (2012) Eur J Org Chem 4412–4419
Liu T, Nair SJ, Lescarbeau A, Belani J, Peluso S, Conley J, Tillotson B, O’Hearn P, Smith S, Slocum K, West K, Helble J, Douglas M, Bahadoor A, Ali J, McGovern K, Fritz C, Palombella VJ, Wylie A, Castro AC, Tremblay MR (2012) J Med Chem 55:8859
Štěpnička P, Solařová H, Císařová I (2011) J Organomet Chem 696:3727
Xia Z, Lv X, Wang W, Wang X (2011) Tetrahedron Lett 52:4906
Sheikh MC, Takagi S, Sakai M, Mori T, Hayashi N, Fujie T, Ono S, Yoshimura T, Morita H (2011) Org Biomol Chem 9:1244
De Wael F, Muccioli GG, Lambert DM, Sergent T, Schneider Y-J, Rees J-F, Marchand-Brynaert J (2010) Eur J Med Chem 45:3564
Vitoriano BC, Carvalho LCR, Estevão MS, Sekera MH, Marques MMB (2010) Synlett 753
Katritzky AR, Khelashvili L, Kovacs J, Shanab K (2009) Chem Biol Drug Des 73:396
Wang X, Li Z, Zhu X, Mao H, Zou X, Kong L, Li X (2008) Tetrahedron 64:6510
Katritzky AR, Chen Q-Y, Tala SR (2008) Org Biomol Chem 6:2400
Kondo T, Sugimoto I, Nekado T, Ochi K, Ohtani T, Tajima Y, Yamamoto S, Kawabata K, Nakai H, Toda M (2007) Bioorg Med Chem 15:2715
Katritzky AR, Abdel-Fattah AAA, Akhmedova RG (2005) Arkivoc 2005:329
Katritzky AR, Hoffman S, Suzuki K (2004) Arkivoc 2004:14
Katritzky AR, Wang Z, Wang M, Wilkerson CR, Hall CD, Akhmedov NG (2004) J Org Chem 69:6617
Katritzky AR, Shestopalov AA, Suzuki K (2004) Synthesis 1806
Katritzky AR, Zhang Y, Singh SK, Steel PJ (2003) Arkivoc 2003:47
Katritzky AR, Abdel-Fattah AAA, Wang M (2003) J Org Chem 68:4932
Katritzky AR, Suzuki K, Singh SK, He HY (2003) J Org Chem 68:5720
Katritzky AR, Yang H, Zhang S, Wang M (2002) Arkivoc 2002:39
Katritzky AR, Wang M, Zhang S, Akhmedov NG (2002) Arkivoc 2002:134
Saravanan V, Muthu Ramalingam B, Mohanakrishnan AK (2014) Eur J Org Chem 2014:1266
Micó XÀ, Vagin SI, Subramanian LR, Ziegler T, Hanack M (2005) Eur J Org Chem 4328
Katritzky AR, Zhang G, Wu J (1994) Synth Commun 24:205
Wyatt P, Hudson A, Charmant J, Orpen AG, Phetmung H (2006) Org Biomol Chem 4:2218
Ryan MD, Harpp DN (1997) Tetrahedron Lett 38:8829
Ryan MD, Harpp DN (1992) Tetrahedron Lett 33:2129
Hermes ME, Marsh FD (1967) J Am Chem Soc 89:4760
Katritzky AR, Akue-Gedu R, Vakulenko AV (2007) Arkivoc 2007:512
Wang YF, Qiu J, Kong D, Gao Y, Lu F, Karmaker PG, Chen FX (2015) Org Biomol Chem 13:365
Adams GL, Carroll PJ, Smith AB (2013) J Am Chem Soc 135:519
Adams GL, Carroll PJ, Smith AB (2012) J Am Chem Soc 134:4037
Suzuki Y, Shimawaki M, Miyazaki E, Osaka I, Takimiya K (2011) Chem Mater 23:795
Hughes TV, Cava MP (1999) J Org Chem 64:313
Cushman M, Mohanakrishnan AK, Hollingshead M, Hamel E (2002) J Med Chem 45:4748
Canterbury DP, Herrick IR, Um J, Houk KN, Frontier AJ (2009) Tetrahedron 65:3165
Drechsler U, Sandman DJ, Foxman BM (2001) J Chem Soc Perkin Trans 2 581
Katritzky AR, Kirichenko N, Rogovoy BV (2003) Arkivoc 2003:8
Katritzky AR, Kirichenko N, Rogovoy BV, Kister J, Tao H (2004) Synthesis 1799
Burckhalter JH, Stephens VC, Hall LAL (1952) J Am Chem Soc 74:3868
Katritzky AR, Rachwal S, Rachwal B (1989) J Org Chem 54:6022
Dumas AM, Bode JW (2012) Org Lett 14:2138
Cho SD, Hwang J, Kim HK, Yim HS, Kim JJ, Lee SG, Yoon YJ (2007) J Heterocycl Chem 44:951
Katritzky AR, Palenik GJ, Anders E, Tropsch JG, Vanden Eynde J-J, Zhang Z (1990) Chem Ber 123:1185
Joshi AA, Viswanathan CL (2006) Bioorg Med Chem Lett 16:2613
Quiclet-Sire B, Zard SZ (2014) Chem Commun 50:5990
Verma AK, Jha RR, Chaudhary R, Tiwari RK, Danodia AK (2013) Adv Synth Catal 355:421
Potapov AS, Chernova NP, Ogorodnikov VD, Petrenko TV, Khlebnikov AI (2011) J Org Chem 7:1526
Cai M, Liang Y, Zhou F, Liu W (2011) J Mater Chem 21:13399
Petit S, Duroc Y, Larue V, Giglione C, Léon C, Soulama C, Denis A, Dardel F, Meinnel T, Artaud I (2009) ChemMedChem 4:261
Greco MN, Hawkins MJ, Powell ET, Almond HR, de Garavilla L, Hall J, Minor LK, Wang Y, Corcoran TW, Di Cera E, Cantwell AM, Savvides SN, Damiano BP, Maryanoff BE (2007) J Med Chem 50:1727
Mobinikhaledi A, Foroughifar N, Goli R (2005) Phosphorus Sulfur Silicon Relat Elem 180:2549
Rádl S, Obadalová I (2005) Arkivoc 2005:4
Gao G-Y, Li DJ, Keung WM (2003) Bioorg Med Chem 11:4069
Katritzky AR, Kirichenko K, Ji Y, Steel PJ, Karelson M (2003) Arkivoc 2003:49
Katritzky AR, Button MAC, Denisenko SN (2001) Heterocycles 54:301
Katritzky AR, Qiu G, Long Q, He H, Steel PJ (2000) J Org Chem 65:9201
Katritzky AR, Fang Y (2000) Heterocycles 53:1783
Katritzky AR, Serdyuk L, Xie L (1998) J Chem Soc Perkin Trans 1 1059
Lu G, Zhan Z, Zhang Y (1998) Synth Commun 28:3657
Zhou J, Bao W, Zhang Y, Wang J (1996) Synth Commun 26:3283
Katritzky AR, Wu H, Xie L, Jiang J (1995) J Heterocycl Chem 32:595
Katritzky AR, Ghiviriga I, Cundy DJ (1994) Heterocycles 38:1041
Katritzky AR, Yang Z, Cundy DJ (1993) Synth Commun 23:3061
Katritzky AR, Hughes CV, Rachwal S (1989) J Heterocycl Chem 26:1579
Katritzky AR, Drewniak-Deyrup M, Lan X, Brunner F (1989) J Heterocycl Chem 26:829
Katritzky AR, Rachwal S, Caster KC, Mahni F, Law KW, Rubio O (1987) J Chem Soc Perkin Trans 1 781
Katritzky AR, Gordeev MF, Greenhill JV, Steel PJ (1992) J Chem Soc Perkin Trans 1 1111
He W, Wang Q, Wang Q, Zhang B, Sun X, Zhang S (2009) Synlett 2009:1311
Wei Y, He W, Liu Y, Liu P, Zhang S (2012) Org Lett 14:704
Li M, Ji N, Lan T, He W, Liu R (2014) RSC Adv 4:20346
Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68:407
Katritzky AR, Ji Y, Fang Y, Prakash I (2001) J Org Chem 66:5613
Pleynet DPM, Dutton JK, Johnson AP (1999) Tetrahedron 55:11903
Katritzky AR, Yao J, Bao W, Qi M, Steel PJ (1999) J Org Chem 64:346
Katritzky AR, Kirichenko K, Ji Y, Prakash I (2002) Chem Heterocycl Compd 38:156
Katritzky AR, Lam JN (1990) Heteroat Chem 1:21
Voronkov MG, Trofimova OM, Brodskaya EI, Bolgova YI, Larina LI, Klyba LV, Zelbst EA, Chernov NF (2003) Arkivoc 2003:125
Roman BI, De Ryck T, Dierickx L, Vanhoecke BWA, Katritzky AR, Bracke M, Stevens CV (2012) Bioorg Med Chem 20:4812
Clark RC, Sang YL, Boger DL (2008) J Am Chem Soc 130:12355
Sang YL, Clark RC, Boger DL (2007) J Am Chem Soc 129:9860
Zrig S, Andrioletti B, Rose E, Colin J (2005) Tetrahedron Lett 46:1103
Katritzky AR, Vvedensky V, Tymoshenko DO (2001) J Chem Soc Perkin Trans 1 2483
Katritzky AR, Zhang S, Hussein AHM, Fang Y, Steel PJ (2001) J Org Chem 66:5606
Katritzky AR, Tymoshenko DO, Monteux D, Vvedensky V, Nikonov G, Cooper CB, Deshpande M (2000) J Org Chem 65:8059
Katritzky AR, Zhang S, Fang Y (2000) Org Lett 2:3789
Johnson AP, Dutton JK, Pleynet DPM (1994) Heterocycles 37:1913
Jha RR, Singh J, Tiwari RK, Verma AK (2013) Arkivoc 2013:228
Tabernor J, Jones LF, Heath SL, Muryn C, Aromi G, Ribas J, Brechin EK, Collison D (2004) Dalton Trans 975
Thomas CM, Therrien B, Neels A, Stœckli-Evans H, Süss-Fink G (2002) J Organomet Chem 658:251
Thomas CM, Neels A, Stœckli-Evans H, Süss-Fink G (2001) Eur J Inorg Chem 2001:3005
Thomas CM, Neels A, Stœckli-Evans H, Süss-Fink G (2001) J Organomet Chem 633:85
Davie CP, Danheiser RL (2005) Angew Chem Int Ed 44:5867
Katritzky AR, Rachwal S, Rachwal B (1987) J Chem Soc Perkin Trans 1 791
Nicolaou KC, Shi L, Lu M, Pattanayak MR, Shah AA, Ioannidou HA, Lamani M (2014) Angew Chem Int Ed 53:10970
Inoue A, Kanematsu M, Mori S, Yoshida M, Shishido K (2013) Synlett 24:61
Lowe JT, Lee MD, Akella LB, Davoine E, Donckele EJ, Durak L, Duvall JR, Gerard B, Holson EB, Joliton A, Kesavan S, Lemercier BC, Liu H, Marié JC, Mulrooney CA, Muncipinto G, Welzel-O’Shea M, Panko LM, Rowley A, Suh BC, Thomas M, Wagner FF, Wei J, Foley MA, Marcaurelle LA (2012) J Org Chem 77:7187
Uno M, Koma Y, Ban HS, Nakamura H (2012) Bioorg Med Chem Lett 22:5169
Fresneda MÁ, Alibés R, Font J, Bayón P, Figueredo M (2012) J Org Chem 77:5030
Li Z, Liu Z, Cho DW, Zou J, Gong M, Breece RM, Galkin A, Li L, Zhao H, Maestas GD, Tierney DL, Herzberg O, Dunaway-Mariano D, Mariano PS (2011) J Inorg Biochem 105:509
Weixler R, Hehn JP, Bach T (2011) J Org Chem 76:5924
Petronijevic FR, Wipf P (2011) J Am Chem Soc 133:7704
Hehn JP, Herdtweck E, Bach T (2011) Org Lett 13:1892
Mahapatra T, Nanda S (2010) Tetrahedron Asymmetry 21:2199
Yoshida M, Shoji Y, Shishido K (2010) Tetrahedron 66:5053
Mahapatra T, Bhunya R, Nanda S (2009) Tetrahedron Lett 50:5392
Degennaro L, Capriati V, Carlucci C, Florio S, Luisi R, Nuzzo I, Cuocci C (2009) Tetrahedron 65:8745
Rehbein J, Leick S, Hiersemann M (2009) J Org Chem 74:1531
Deguest G, Bischoff L, Fruit C, Marsais F (2007) Org Lett 9:1165
De la Reberdière A, Lachaud F, Chuburu F, Cadiou C, Lemercier G (2012) Tetrahedron Lett 53:6115
Altman RA, Nilsson BL, Overman LE, De Alaniz JR, Rohde JM, Taupin V (2010) J Org Chem 75:7519
Katritzky AR, Singh S, Mohapatra PP, Clemens N, Kirichenko K (2005) Arkivoc 2005:63
Katritzky AR, Huang TB, Voronkov MV, Wang M, Kolb H (2000) J Org Chem 65:8819
Pearson WH, Stevens EP (1998) J Org Chem 63:9812
Katritzky AR, Ignatchenko AV, Lang H (1995) J Org Chem 60:4002
Katritzky AR, Yao G, Lan X, Zhao X (1993) J Org Chem 58:2086
Katritzky AR, Gordeev MF (1991) J Chem Soc Perkin Trans 1 2199
Katritzky AR, Latif M, Urogdi L (1990) J Chem Soc Perkin Trans 1 667
Katritzky AR, Rao MSC (1990) Synthesis 663
Katritzky AR, Rao MSC (1989) J Chem Soc Perkin Trans 1 2297
Aurrecoechea JM, Bustos F, López B, Saornil C, Suero R (2009) Arkivoc 2009:94
Aurrecoechea JM, Suero R, De Torres E (2006) J Org Chem 71:8767
Dong Y, Sun J, Wang X, Xu X, Cao L, Hu Y (2004) Tetrahedron Asymmetry 15:1667
Lee C-H, Yang ID, Lee J-D, Nakamura H, Ko J, Kang SO (2004) Synlett 1799
Katritzky AR, Jain R, Akhmedova R, Xu YJ (2003) Arkivoc 2003:4
Bustos F, Gorgojo JM, Suero R, Aurrecoechea JM (2002) Tetrahedron 58:6837
Abonia R, Albornoz A, Insuasty B, Quiroga J, Meier H, Hormaza A, Nogueras M, Sanchez A, Cobo J, Low JN (2001) Tetrahedron 57:4933
Locher C, Peerzada N (2000) Arkivoc 2000:14
Walz AJ, Sundberg RJ (2000) J Org Chem 65:8001
Locher C, Peerzada N (1999) J Chem Soc Perkin Trans 1 179
Katritzky AR, Belyakov SA, Sorochinsky AE, Steel PJ, Schall OF, Gokel GW (1996) J Org Chem 61:7585
Katritzky AR, Denisko OV, Belyakov SA, Schall OF, Gokel GW (1996) J Org Chem 61:7578
Katritzky AR, Allin SM (1995) Synth Commun 25:2751
Sechi M, Rizzi G, Bacchi A, Carcelli M, Rogolino D, Pala N, Sanchez TW, Taheri L, Dayam R, Neamati N (2009) Bioorg Med Chem 17:2925
Katritzky AR, Serdyuk L, Xie L, Ghiviriga I (1997) J Org Chem 62:6215
Katritzky AR, Toader D, Xie L (1996) J Org Chem 61:7571
Katritzky AR, El-Zemity S, Lang H (1995) J Chem Soc Perkin Trans 1 3129
Katritzky AR, Xie L, Cundy D (1995) Synth Commun 25:539
Katritzky AR, Lan X, Lam JN (1991) Chem Ber 124:1819
Katritzky AR, Lan X, Lam JN (1991) Chem Ber 124:1809
Katritzky AR, Lan X, Lam JN (1990) Synthesis 341
Katritzky AR, Drewniak M (1988) J Am Chem Soc 2339
Katritzky AR, He H-Y, Jiang R, Long Q (2001) Tetrahedron Asymmetry 12:2427
Katritzky AR, Abonia R, Yang B, Qi M, Insuasty B (1998) Synthesis 1487
Juliusz P, Lucyna M (1994) Heterocycles 37:311
Quan ZJ, Ren RG, Jia XD, Da YX, Zhang Z, Wang XC (2011) Tetrahedron 67:2462
Katritzky AR, Zhao X, Shcherbakova IV (1991) J Chem Soc Perkin Trans 1 3295
Katritzky AR, Huang Z, Fang Y, Prakash I (1999) J Org Chem 64:2124
Katritzky AR, Zhang Z, Lang H, Xie L (1998) Heterocycles 47:187
Katritzky AR, Wang J, Karodia N, Li J (1997) J Org Chem 62:4142
Katritzky AR, Wang Z, Lang H, Feng D (1997) J Org Chem 62:4125
Katritzky AR, Xie L, Serdyuk L (1996) J Org Chem 61:7564
Katritzky AR, Wang Z, Lang H (1996) Organometallics 15:486
Katritzky AR, Yang Z, Moutou JL (1995) Tetrahedron Lett 36:841
Degl’Innocenti A, Capperucci A, Oniciu DC, Katritzky AR (2000) J Org Chem 65:9206
Hammaecher C, Bouillon JP, Portella C (2009) Tetrahedron 65:5527
Noda H, Erős G, Bode JW (2014) J Am Chem Soc 136:5611
Katritzky AR, Qi M, Feng D, Nichols DA (1997) J Org Chem 62:4121
Bachman GB, Heisey LV (1946) J Am Chem Soc 68:2494
Toulot S, Bonnin Q, Comte V, Adriaenssens L, Richard P, Le Gendre P (2013) Eur J Org Chem 2013:736
Katritzky AR, Rachwal B, Rachwal S (1995) J Org Chem 60:7631
Katritzky AR, Fan WQ, Long QH (1993) Synthesis 229
Katritzky AR, Yannakopoulou K, Lue P, Rasala D, Urogdi L (1989) J Chem Soc Perkin Trans 1 225
Katritzky AR, Rachwal B, Rachwal S (1995) J Org Chem 60:3993
Katritzky AR, Yannakopoulou K, Kuzmierkiewicz W, Aurrecoechea JM, Palenik GJ, Koziol AE, Szczesniak M (1987) J Chem Soc Perkin Trans 1 2673
Xu S, Zakharov LN, Liu S-Y (2011) J Am Chem Soc 133:20152
Piller FM, Bresser T, Fischer MKR, Knochel P (2010) J Org Chem 75:4365
Katritzky AR, Abdel-Fattah AAA, Steel PJ (2006) Tetrahedron Lett 47:1465
Kopp F, Sklute G, Polborn K, Marek I, Knochel P (2005) Org Lett 7:3789
Katritzky AR, Nair SK, Qiu G (2002) Synthesis 199
Churlaud C, Pornet J, Oniciu DC, Katritzky AR (1999) Organometallics 18:4270
Ahn JH, Joung MJ, Yoon NM, Oniciu DC, Katritzky AR (1999) J Org Chem 64:488
Love BE, Nguyen BT (1998) Synlett 1123
Katritzky AR, Nichols DA, Qi M (1998) Tetrahedron Lett 39:7063
Katritzky AR, Strah S, Belyakov SA (1998) Tetrahedron 54:7167
Katritzky AR, Nichols DA, Qi M, Yang B (1997) J Heterocycl Chem 34:1259
Bao W, Zhang Y (1997) Synth Commun 27:615
Katritzky AR, Rachwal S, Rachwal B (1994) J Org Chem 59:5206
Katritzky AR, Belyakov SA, Dupont Durst H, Xu R, Dalal NS (1994) Can J Chem 72:1849
Bulman Page PC, Allin SM, Collington EW, Carr RAE (1993) J Org Chem 58:6902
Katritzky AR, Rachwal B, Rachwal S (1993) J Org Chem 58:812
Katritzky AR, Rachwal S, Rachwal B, Steel PJ (1992) J Org Chem 57:4932
Katritzky AR, Gallos JK, Yannakopoulou K (1989) Synthesis 31
Katritzky AR, Gordeev MF (1993) J Org Chem 58:4049
Katritzky AR, Abdel-Fattah AAA, Celik I (2007) Arkivoc 2007:96
Katritzky AR, Belyakov SA, Sorochinsky AE, Henderson SA, Chen J (1997) J Org Chem 62:6210
Al-Soud YA, Al-Masoudi NA, Ferwanah AERS (2003) Bioorg Med Chem 11:1701
Sanna P, Carta A, Nikookar MER (2000) Eur J Med Chem 35:535
Yu T, Zhao M, Li A, Zhao Y, Zhang H, Fan D (2013) Res Chem Intermed 39:2259
Das J, Rao CVL, Sastry TVRS, Roshaiah M, Sankar PG, Khadeer A, Kumar MS, Mallik A, Selvakumar N, Iqbal J, Trehan S (2005) Bioorg Med Chem Lett 15:337
Carta A, Sanna P, Palomba M, Vargiu L, La Colla M, Loddo R (2002) Eur J Med Chem 37:891
Carta A, Sanna P, Bacchi A (2002) Heterocycles 57:1079
Dutton JK, Pleynet DPM, Johnson AP (1999) Tetrahedron 55:11927
Paluchowska MH, Bojarski AJ, Bugno R, Charakchieva-Minol S, Wesołowska A (2003) Arch Pharm 336:104
Henke BR, Drewry DH, Jones SA, Stewart EL, Weaver SL, Wiethe RW (2001) Bioorg Med Chem Lett 11:1939
Katritzky AR, Serdyuk L, Chassaing C, Toader D, Wang X, Forood B, Flatt B, Sun C, Vo K (2000) J Comb Chem 2:182
Al-Omran F, Abd El-Hay OY, El-Khair AA (2000) J Heterocycl Chem 37:1617
Zhang Z, Yin Z, Kadow JF, Meanwell NA, Wang T (2004) Synlett 2323
Ali OM, Amr AE-GE, Mostafa EE (2014) Res Chem Intermed 40:1545
Katritzky AR, Aslan D, Shcherbakova IV, Chen J, Belyakov S (1996) J Heterocycl Chem 33:1107
Al-Jalal NA, Ibrahim MR, Al-Awadi NA, Elnagdi MH, Ibrahim YA (2014) Molecules 19:20695
Katritzky AR, Li J, Malhotra N (1992) Liebigs Ann Chem 843
Katritzky AR, Zhang GF, Fan WQ, Wu F, Pernak J (1993) J Phys Org Chem 6:567
Katritzky AR, Oniciu DC, Ghiviriga I (1997) Synth Commun 27:1613
Yan W, Liao T, Tuguldur O, Zhong C, Petersen JL, Shi X (2011) Chem Asian J 6:2720
Basu B, Paul S, Nanda AK (2009) Green Chem 11:1115
Katritzky AR, Yao J, Denisko OV (2000) J Org Chem 65:8063
Katritzky AR, Yao J, Yang B (1999) J Org Chem 64:6066
Katritzky AR, Yao J, Qi M (1998) J Org Chem 63:5232
Katritzky AR, Cheng D, Henderson SA, Li J (1998) J Org Chem 63:6704
Katritzky AR, Ferwanah AERS, Denisenko SN (1999) Heterocycles 50:767
Katritzky AR, Wang X, Denisenko A (2001) J Org Chem 66:2850
Katritzky AR, Button MAC, Denisenko SN (2000) J Heterocycl Chem 37:1505
Katritzky AR, Pleynet DPM, Yang B (1997) J Org Chem 62:4155
Orth RE, Soedigdo S (1965) J Heterocycl Chem 2:486
Katritzky AR, Tao H, Kirichenko K (2007) Arkivoc 2007:142
Nieuwenhuijzen JW, Conti PGM, Ottenheijm HCJ, Linders JTM (1998) Tetrahedron Lett 39:7811
Korhonen J, Kuusisto A, van Bruchem J, Patel JZ, Laitinen T, Navia-Paldanius D, Laitinen JT, Savinainen JR, Parkkari T, Nevalainen TJ (2014) Bioorg Med Chem 22:6694
Harpp DN, MacDonald JG, Larsen C (1985) Can J Chem 63:951
Tiwari VK, Kale RR, Mishra BB, Singh A (2008) Arkivoc 2008:27
Tiwari VK, Singh DD, Hussain HA, Mishra BB, Singh A (2008) Monatsh Chem 139:43
Tiwari VK, Singh A, Hussain HA, Mishra BB, Tripathi V (2007) Monatsh Chem 138:653
Katritzky AR, Khashab NM, Haase DN, Yoshioka M, Ghiviriga I, Steel PJ (2007) J Org Chem 72:6742
Katritzky AR, Khashab NM, Bobrov S, Yoshioka M (2006) J Org Chem 71:6753
Kumar D, Singh AS, Tiwari VK (2015) RSC Adv 5:31584
Kumar D, Mishra A, Mishra BB, Bhattacharya S, Tiwari VK (2013) J Org Chem 78:899
Katritzky AR, Meher G, Narindoshvili T (2009) Collect Czechoslov Chem Commun 74:1061
Thambidurai S, Jeyasubramanian K, Ramalingam SK (1996) Polyhedron 15:4011
Katritzky AR, Rogovoy BV, Chassaing C, Vvedensky V (2000) J Org Chem 65:8080
Schell P, Richards MP, Hanson K, Berk SC, Makara GM (2005) J Comb Chem 7:96
Katritzky AR, Rogovoy BV, Vvedensky V, Kovalenko K, Forood B (2002) J Comb Chem 4:290
Katritzky AR, Vvedensky V, Cai X, Rogovoy BV, Steel PJ (2002) Arkivoc 2002:82
Katritzky AR, Rogovoy BV, Cai X, Kirichenko N, Kovalenko KV (2004) J Org Chem 69:309
Katritzky AR, Rogovoy BV, Vvedensky V, Kovalenko K, Steel PJ, Markov VI, Forood B (2001) Synthesis 897
Katritzky AR, Huang L, Chahar M, Sakhuja R, Hall CD (2012) Chem Rev 112:1633
Schade D, Kotthaus J, Klein N, Kotthaus J, Clement B (2011) Org Biomol Chem 9:5249
Katritzky AR, Arend M (1998) J Org Chem 63:9989
Katritzky AR, Denisenko A, Arend M (1999) J Org Chem 64:6076
Katritzky AR, Denisenko A, Denisenko SN (2000) J Heterocycl Chem 37:1309
Katritzky AR, Huang TB, Voronkov MV (2000) J Org Chem 65:2246
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Gérardy, R., Monbaliu, JC.M. (2015). Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives. In: Monbaliu, JC. (eds) The Chemistry of Benzotriazole Derivatives. Topics in Heterocyclic Chemistry, vol 43. Springer, Cham. https://doi.org/10.1007/7081_2015_179
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