Methods for the synthesis of haloimidazoles (review)

M. D. Mashkovskii, Drugs [in Russian], Novaya Volna, Moscow (2005), p. 444.Google Scholar

M. Ogawa and A. Nishimura, Eur. Pat. Application No. 1417887, Ref. Zh. Khim., 04.18-190.271P (2004).Google Scholar

K. Hofmann, Imidazole and its Derivatives. Interscience, New York, Interscience, London (1953), Pt. I.Google Scholar

E. Schipper and A. Day, in: R. Elderfield (editor), Heterocyclic Compounds [Russian translation], Izd. Inostr. Lit., Moscow (1962), Vol. 5, p. 161.Google Scholar

P. Bouchet, C. Coquelet, and J. Elguego, Bull. Soc. Chim. Fr., 171 (1977).Google Scholar

B. Iddon, Heterocycles, 23, 417 (1985).CrossRefGoogle Scholar

R. C. Patterson, A. DiMaggio, A. L. Hebert, T. J. Haley, J. P. Mikitka, and I. M. Sarkar, J. Org. Chem., 36, 631 (1971).CrossRefGoogle Scholar

J. Kraupa, Chem. Listy, 67, 1035 (1973).Google Scholar

K. L. Kirk and L. A. Cohen, J. Am. Chem. Soc., 93, 3060 (1971).CrossRefGoogle Scholar

K. L. Kirk and L. A. Cohen, J. Am. Chem. Soc., 95, 4619 (1973).CrossRefGoogle Scholar

F. Farba, C. Gálvez, A. González, P. Viladoms, and J. Vilarrasa, J. Heterocycl. Chem., 15, 1227 (1978).CrossRefGoogle Scholar

J. Vilarrasa, C. Galvez, and M. Callaffel, Anal. Quim., 71, 631 (1975); Chem. Abstr., 83, 178919 (1975).Google Scholar

Y. Takeuchi, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 44, 4240 (1979).CrossRefGoogle Scholar

Y. Takeuchi, K. L. Kirk, and L. A. Cohen, J. Org. Chem., 43, 3570 (1978).CrossRefGoogle Scholar

M. E. Borai, A. N. Moustafa, M. Anwar, and F. I. Abdel Hay, Pol. J. Chem., 55, 1659 (1981).Google Scholar

N. S. Mani, J. A. Jablonowski, and T. K. Jones, J. Org. Chem., 69, 8115 (2004).CrossRefGoogle Scholar

K. L. Kirk, W. Nagai, and L. A. Cohen, J. Am. Chem. Soc., 95, 8389 (1973).CrossRefGoogle Scholar

W. A. Sheppard and O. W. Webster, J. Am. Chem. Soc., 95, 2695 (1973).CrossRefGoogle Scholar

O. W. Webster, Ger. Pat. Appl. 2317453; Chem. Abstr., 83, 14926 (1974).Google Scholar

E. C. Coard, Liu Hui, and P. G. Rasmussen, Tetrahedron, 55, 2811 (1999).CrossRefGoogle Scholar

K. L. Kirk and L. A. Cohen, J. Org. Chem., 38, 3647 (1973).CrossRefGoogle Scholar

T. Chandra, X. Zou, E. J. Valente, and K. L. Brown, J. Org. Chem., 71, 5000 (2006).CrossRefGoogle Scholar

K. Burger, R. Ottinger, H. Goth, and J. Firl, Chem. Ber., 115, 2494 (1982).CrossRefGoogle Scholar

B. Dolensky, Y. Takeuchi, L. A. Cohen, and K. L. Kirk, J. Fluor. Chem., 107, 147 (2001).CrossRefGoogle Scholar

J. Garcia and J. Vilarrasa, Heterocycles, 27, 1803 (1988).CrossRefGoogle Scholar

N. R. Jena, P. S. Kushwaha, and P. S. Mishra, J. Comput. Chem., 29, 98 (2008).CrossRefGoogle Scholar

R. K. Shukla and P. C. Mishra, J. Phys. Chem. B, 112, 7925 (2008).CrossRefGoogle Scholar

J. L. Imbach, R. Jacquier, and A. Romane, J. Heterocycl. Chem., 4, 451 (1967).CrossRefGoogle Scholar

G. N. Tyurenkova, and N. P. Bednyagina, in: Methods for the Production of Chemical Reagents and Preparations [in Russian], IREA, Moscow (1967), No. 15, p. 173.Google Scholar

C. P. Whittle, Aust. J. Chem., 33, 1545 (1980).CrossRefGoogle Scholar

N. P. Bednyagina, G. N. Tyurenkova, and I. V. Panov, Zh. Obshch. Khim., 34, 1575 (1964).Google Scholar

H. Rutz, K. Gubler, South African Pat. 6802643; Chem. Abstr., 71, 38964 (1969).Google Scholar

A. W. Lutz, S. Delorenzo, J. Heterocycl. Chem., 4, 399 (1967).CrossRefGoogle Scholar

P. M. Kochergin, Khim. Geterotsikl. Soedin., 398 (1965). [Chem. Heterocycl. Comp., 1, 265 (1965)].Google Scholar

P. M. Kochergin and M. A. Klykov, USSR Inventor's Certificate 232270; Byul. Izobr., No. 1, 28 (1969).Google Scholar

J. P. Dirlam, R. B. James, and E. V. Shoop, J. Heterocycl. Chem., 17, 409 (1980).CrossRefGoogle Scholar

J. P. Dirlam, R. B. James, and E. V. Shoop, J. Org. Chem., 47, 2196 (1982).CrossRefGoogle Scholar

J. J. Baldwin, R. K. Lumma, F. C. Novello, G. S. Ponticello, J. M. Spraque, and D. E. Duggan, J. Med. Chem., 20, 1189 (1977).CrossRefGoogle Scholar

C. Almansa, J. Alfón, A. F. de Arriba, F. L. Cavalcanti, I. Escamilla, L. A. Gómez, A. Miralles, R. Soliva, J. Bartrolí, E. Carceller, M. Merlos, and J. García-Rafanell, J. Med. Chem., 46, 3463 (2003).CrossRefGoogle Scholar

C. Almansa, J. Bartroli, J. Billoc, F. L. Cavalcanti, R. Ferrando, L. A. Gomez, I. Ramis, E. Carieller, M. Merlos, and J. Garcia-Rafanell, J. Med. Chem., 47, 5579 (2004).CrossRefGoogle Scholar

K. Srinivas, N. C. K. Snehalatha, S. Ramesh, and M. Pardhasatadhi, Synthesis, 506 (2004).Google Scholar

J. Sundermeger and H. W. Roesky, Angew. Chem., 100, 1417 (1988).CrossRefGoogle Scholar

P. M. Kochergin, Zh. Obshch. Khim., 34, 2735 (1964).Google Scholar

P. M. Kochergin and R. M. Palei, Zh. Obshch. Khim., 38, 1132 (1968).Google Scholar

G. E. Trout and P. R. Levy, Rec. Trav. Chim. Pays-Bas, 85, 765 (1966).CrossRefGoogle Scholar

G. E. Trout and P. R. Levy, Rec. Trav. Chim. Pays-Bas, 84, 1257 (1965).CrossRefGoogle Scholar

E. F. Godefroi, C. A. M. van der Eycken, and P. A. J. Janssen, J. Org. Chem., 32, 1259 (1967).CrossRefGoogle Scholar

P. M. Kochergin, Zh. Obshch. Khim., 34, 3402 (1964).Google Scholar

P. M. Kochergin, Author’s Abstract of Thesis for Doc. Chem. Sci. [in Russian], Moscow (1968).Google Scholar

P. M. Kochergin, Khim. Geterotsikl. Soedin., 402 (1965). [Chem. Heterocycl. Comp., 1, 268 (1965)].Google Scholar

V. S. Korsunskii, P. M. Kochergin, and V. S. Shlikhunova, Zh. Org. Khim., 26, 82 (1990).Google Scholar

V. S. Korsunskii, P. M. Kochergin, and V. S. Shlikhunova, USSR Inventor's Certificate 445649; Byul. Izobr., No. 37, 61 (1974).Google Scholar

F. King, J. Clark-Lewis, D. Ridd, and G. Smith, J. Chem. Soc., 1039 (1954).Google Scholar

V. S. Korsunskii, P. M. Kochergin, and V. S. Shlikhunova, USSR Inventor's Certificate 437765; Byul. Izobr., No. 28, 53 (1974).Google Scholar

V. S. Korsunskii, P. M. Kochergin, and V. S. Shlikhunova, Khim.-Farm. Zh., 24, No. 5, 56 (1990).Google Scholar

P. M. Kochergin, Khim. Geterotsikl. Soedin., 754 (1965). [Chem. Heterocycl. Comp., 1, 511 (1965)].Google Scholar

K. Shimada, J. Pharm. Soc. Jpn., 91, 221 (1971).Google Scholar

D. S. Noyce and G. T. Stowe, J. Org. Chem., 38, 3762 (1973).CrossRefGoogle Scholar

G. B. Barlin, J. Chem. Soc. (B), 641 (1967).Google Scholar

P. B. W. McCallum, M. R. Grimmett, A. G. Blackman, and R. T. Weavers, Aust. J. Chem., 52, 159 (1999); Ref. Zh. Khim., 00.07-19Zh.240 (2000).Google Scholar

G. L. Schmir and L. A. Cohen, Biochemistry, 4, 533 (1965).CrossRefGoogle Scholar

K. E. Stensio, K. Wahlberg, and R. Wahren, Acta Chem. Scand., 27, 2179 (1973).CrossRefGoogle Scholar

T. J. Benson and B. Robinson, J. Chem. Soc., Perkin Trans. 1, 211 (1992).Google Scholar

B. D. Palmer and W. A. Denny, J. Chem. Soc., Perkin Trans. 1, 95 (1989).Google Scholar

V. Calo, L. Lopez, F. Naso, and P. E. Todeseo, J. Chem. Soc., Perkin Trans. 1, 2567 (1972).Google Scholar

G. C. Lancini, N. Maggi, and P. Sensi, Farmaco, Ed. Sci., 18, 390 (1963).Google Scholar

P. M. Kochergin, A. M. Tsyganova, L. M. Viktorova, and E. M. Peresleni, Khim. Geterotsikl. Soedin., Coll. 1, Nitrogen-Containing Heterocycles [in Russian] (1967), p. 126.Google Scholar

G. U. Baig and M. F. G. Stevens, J. Chem. Soc., Perkin Trans. 1, 665 (1987).Google Scholar

A. L. Kanibolotskii, V. A. Mikhailov, and V. A. Savelova, Zh. Org. Khim., 32, 1589 (1996).Google Scholar

K. L. Kirk, J. Org. Chem., 43, 4381 (1978).CrossRefGoogle Scholar

R. M. de Figueiredo, S. Thoret, C. Huet, and J. Dubois, Synthesis, 529 (2007).Google Scholar

W. E. Allen, Ch. J. Fowler, V. M. Lynch, and L. L. Sessler, Chem. Eur. J., 7, 721 (2001).CrossRefGoogle Scholar

M. Moreno-Manas, J. Bassa, N. Liado, and R. J. Pleixtats, J. Heterocycl. Chem., 27, 673 (1990).CrossRefGoogle Scholar

M. A. Clyne and F. Aldabbagh, Org. Biomol. Chem., 4, 268 (2006).CrossRefGoogle Scholar

H. Pauly and K. Gundermann, Ber., 41, 3999 (1908).Google Scholar

H. Pauly and K. Gundermann, Ber., 43, 2243 (1910).Google Scholar

H. Pauly and E. Aranner, J. prakt. Chem. [2], 118, 33 (1928).CrossRefGoogle Scholar

J. H. Ridd, J. Chem. Soc., 1238 (1955).Google Scholar

M. Hoffer, V. Toome, and A. Brossi, J. Heterocycl. Chem., 3, 454 (1966).CrossRefGoogle Scholar

E. Winkelman, W. Raether, U. Gebert, and A. Sinharay, Arzneim.-Forsch., 27 (II), 2251 (1977).Google Scholar

H. B. Bensusan and M. S. R. Naidu, Biochemistry, 6, 12 (1967).CrossRefGoogle Scholar

M. S. R. Naidu, and H. B. Bensusan, J. Org. Chem., 33, 1307 (1968).CrossRefGoogle Scholar

N. J. Hasking, G. C. Ford, K. A. Waddell, J. P. Dickens, R. L. Dyer, R. J. Hamill, and T. A. Harrow, Biomed. Mass. Spectrometry, 8, 351 (1981).CrossRefGoogle Scholar

J. P. Dickens, R. L. Dyer, R. J. Hamill, and T. A. Harrow, J. Chem. Soc., Chem. Commun., 523 (1979).Google Scholar

J. P. Dickens, R. L. Dyer, R. J. Hamill, T. A. Harrow, R. H. Bible, P. M. Finnegan, K. Henrick, and P. G. Owston, J. Org. Soc., 46, 1781 (1981).CrossRefGoogle Scholar

V. Sudarsuman, K. Nagarajan, T. George, S. J. Shenoy, V. V. Iyer, and A. P. Kaulgud, Ind. J. Chem., 21B, 1022 (1982).Google Scholar

C. T. Holloway, R. P. M. Bond, J. G. Knight, and R. B. Beechey, Biochemistry, 6, 19 (1967).CrossRefGoogle Scholar

S. S. Novikov, L. I. Khmel’nitskii, O. V. Lebedev, L. V. Epishina, and V. V. Sevast'yanova, Khim. Geterotsikl. Soedin., 664 (1970). [Chem. Heterocycl. Comp., 6, 614 (1970)].Google Scholar

K. L. Kirk, J. Heterocycl. Chem., 22, 57 (1985).CrossRefGoogle Scholar

P. J. Garegg, R. Johanson, C. Ortega, and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 681 (1982).Google Scholar

M. S. Shvartsberg, L. N. Bizhan, A. N. Sinyakov, and N. R. Myasnikov, Izv. Akad. Nauk SSSR, Ser. Khim., 1563 (1979).Google Scholar