Synthesis of novel derivatives of 2-(azolylimino)thiazoline / Eltsov O.S., Mokrushin V.S., Tkachev A.V. // Russian Chemical Bulletin. - 2004. - V. 53, l. 10. - P. 2293-2302.

ISSN:

10665285

Type:

Article

Abstract:

Successive alkylation of 5-(3-phenylthioureido)-3H-imidazole-4-carboxamides with alkyl halides and chloroacetone gave (N-oxopropylimidazolyl)isothioureas, which were easily converted into derivatives of purine and imidazopyrazinone. In the case of ethyl 5-(3-phenylthioureido)-3H-imidazole-4-carboxylate, primary alkylation occurs at the N atom of the imidazole ring. Reactions of 5-(3-phenylthioureido)-3H-imidazole-4-carboxamides with haloketones afforded a number of 4-hydroxy-2-imidazolyliminothiazolidines and 2-imidazolylimino- Δ4-thiazolines. © 2004 Springer Science+Business Media, Inc.

Author keywords:

(N-alkylimidazolyl)isothioureas; 2-imidazolylimino-Δ4-thiazolines; Alkyl halides; Alkylation; Haloketone; Imidazo[5,1-c]pyrazin-7-ones; Imidazolylthiourea; Purine derivatives

Index keywords:

acetone; amide; halide; imidazole derivative; imidazopyrazine derivative; purine; thiazole derivative; thiourea derivative; alkylation; article; chemical reaction kinetics; drug structure; drug synthe

DOI:

10.1007/s11172-005-0116-8

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-21644438588&doi=10.1007%2fs11172-005-0116-8&partnerID=40&md5=ba6ce198d92891bf255458ea2ef2c7a9

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Другие поля

Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-21644438588&doi=10.1007%2fs11172-005-0116-8&partnerID=40&md5=ba6ce198d92891bf255458ea2ef2c7a9
Affiliations	Ural State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation; N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090 Novosibirsk, Russian Federation
Author Keywords	(N-alkylimidazolyl)isothioureas; 2-imidazolylimino-Δ4-thiazolines; Alkyl halides; Alkylation; Haloketone; Imidazo[5,1-c]pyrazin-7-ones; Imidazolylthiourea; Purine derivatives
Chemicals/CAS	acetone, 67-64-1; amide, 17655-31-1; purine, 120-73-0
References	Habib, N.S., Rida, S.M., Badawey, E.A.M., Fahmy, N.T.Y., Ghozlan, H.A., (1997) Pharmazie, 51, p. 346; Al-Rashood, Khalid, A., Bayomi, S.M., (1991) Sulfur Lett., 13 (4), p. 151; Griffin, T.S., Woods, T.S., Klayman, D.L., (1975) Adv. Heterocycl. Chem., 18, p. 99; Eltsov, O.S., Mokrushin, V.S., Rybalova, T.V., Gatilov, Y.V., Tkachev, A.V., (2000) Mendeleev Commun., p. 233; Pimentel, G.C., McClellan, A.L., (1960) The Hydrogen Bond, 455p. , Ed. L. Pauling, London; Bellamy, L.J., (1954) The Infra-Red Spectra of Complex Molecules, 580p. , Wiley, New York; Bellamy, L.J., (1968) Advances in Infrared Group Frequencies, 309p. , Methuen, Suffolk; Shaw, E., Woolley, D.W., (1949) J. Biol. Chem., 181, p. 89; Pushkareva, Z.V., Ofitserov, V.I., Mokrushin, V.S., Aglitskaya, K.V., (1975) Khim. Geterotsikl. Soedin., 8, p. 1141; (1975) Chem. Heterocycl. Chem., 8. , Engl. Transl; Robinson, B., Sheperd, D.M., (1962) J. Pharm. Pharmacol., 14, p. 9; Kulev, L.P., Gireva, R.N., (1957) Zh. Prikl. Khim., 30 (5), p. 811
Correspondence Address	Eltsov, O.S.; Ural State Technical University, 19 ul. Mira, 620002 Ekaterinburg, Russian Federation; email: eltsov@htf.ustu.ru
Language of Original Document	English
Abbreviated Source Title	Russ. Chem. Bull.
Source	Scopus