5,7-Substituted thiazolo[2,3-a]pyrimidines: Synthesis, stereochemistry and crystal structure / Yaremenko F., Beryozkina T., Khvat A., Svidlo I., Shishkin O., Shishkina S., Orlov V. // Journal of Molecular Structure. - 2008. - V. 874, l. 1-3. - P. 57-63.

ISSN:

00222860

Type:

Article

Abstract:

Reaction of 2-aminothiazoline (1) with α,β-unsaturated carbonyl compounds 2 under mild conditions (acetone, room temperature) gives two diastereomers 5-R-7-hydroxy-5H-tetrahydrothiazolo[2,3-a]pyrimidines 3. According to 1H NMR, major isomers of 3 have axial OH-groups whereas minor isomers have equatorial OH-groups. The X-ray investigation of compound 3i reveals only A type diastereomer in the crystal phase. The asymmetric unit contains two forms (A1 and A2) with slightly different geometrical parameters. Each of them consists of a pair of enantiomers E1 and E2. As a result, the asymmetric unit contains the centrosymmetric dimers (A1E1 ... A1E2 and A2E2 ... A2E1), due to the intermolecular hydrogen bonds. 5,7-Diaryl-5H-2,3-dihydrothiazolo[2,3-a]pyrimidines 4 were obtained via reaction of 1 with 2 under stronger conditions (DMF or chloroform, heating). Structure of product 4p was confirmed by X-ray structural analysis. © 2007 Elsevier B.V. All rights reserved.

Author keywords:

2-Aminothiazoline; NMR spectroscopy; Thiazolo[2,3-a]pyrimidines; X-ray structural analysis

Index keywords:

Acetone; Crystal structure; Nuclear magnetic resonance spectroscopy; Reaction kinetics; Stereochemistry; Synthesis (chemical); X ray analysis; Aminothiazoline; Pyrimidines; X ray structural analysis;

DOI:

10.1016/j.molstruc.2007.03.031

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-38649138323&doi=10.1016%2fj.molstruc.2007.03.031&partnerID=40&md5=73a1d8fa633300b05a2f8fa008a5a7ca

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Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-38649138323&doi=10.1016%2fj.molstruc.2007.03.031&partnerID=40&md5=73a1d8fa633300b05a2f8fa008a5a7ca
Affiliations	V. Ya. Danilevsky Institute of Endocrine Pathology Problems, Academy of Medicinal Sciences of Ukraine, 4 Artema Str, 61002 Kharkiv, Ukraine; V. N. Karazin Kharkiv National University, 4 Svobody Sq, 61077 Kharkiv, Ukraine; ChemDiv. Inc., 11558 Sorrento Valley Rd., Suites San Diego, CA 92121, United States; SSI 'Institute for Single Crystals' National Academy of Science of Ukraine, 60 Lenina Ave, 61001 Kharkiv, Ukraine
Author Keywords	2-Aminothiazoline; NMR spectroscopy; Thiazolo[2,3-a]pyrimidines; X-ray structural analysis
References	Chebanov, V.A., Desenko, S.M., (2006) Curr. Org. Chem., p. 297; Proskuryakov, S.Ya., Konoplyannikov, A.G., Skvortzov, V.G., Mandrugin, A.A., Fedoseev, V.M., (2005) Russ. Chem. Rev., 74, p. 859; Simkeviciene, V., Straukas, J., Uleckiene, S., (2002) Acta Biol. Hung., 53, p. 293; Vrasidas, I., Kemmink, J., Liskamp, R.M.J., Pieters, R.J., (2002) Org. Lett., 4, p. 1807; Baxter, A., Cooper, A., Kinchin, E., Moakes, K., Unit, J., Wallace, A., (2006) Bioorg. Med. Chem. Lett., 16, p. 960; Holla, B.S., Rao, B.S., Sarojini, B.K., Akberali, P.M., (2004) Eur. J. Med. Chem., 39, p. 777; Joly, P., Divorne, C., Roggero, J., (1970) C.R. Acad. Sc. Paris Serie C, 271, p. 875; Hohenberg, P., Kohn, W., (1964) Phys. Rev. B, 136, p. 864; Kohn, W., Sham, L., (1965) J. Phys. Rev. A, 140, p. 1133; Parr, R.G., Yang, W., (1989) Density-functional Theory of Atoms and Molecules, , Oxford Univ. Press, Oxford; Woon, D.E., Dunning, T.H., (1993) J. Chem. Phys., 98, p. 1358; Zefirov, N.S., Palyulin, V.A., Dashevskaya, E.E., (1990) J. Phys. Org. Chem., 3, p. 147; Zefirov, Yu.V., Zorky, P.M., (1989) Usp. Khim., 58, p. 713
Correspondence Address	Orlov, V.; V. N. Karazin Kharkiv National University, 4 Svobody Sq, 61077 Kharkiv, Ukraine; email: orlov@univer.kharkov.ua
CODEN	JMOSB
Language of Original Document	English
Abbreviated Source Title	J. Mol. Struct.
Source	Scopus