Combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions as a versatile route to pyrimidines bearing thiophene fragments / Verbitskiy Egor V.,Cheprakova Ekaterina M.,Slepukhin Pavel A.,Kodess Mikhail I.,Ezhikova Marina A.,Pervova Marina G.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // TETRAHEDRON. - 2012. - V. 68, l. 27-28. - P. 5445-5452.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

It has been shown that combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen is a versatile method for the synthesis of 4-(thiophen-2-yl)-, 5-(thiophen-2-yl)-, and 4,5-di(thiophen-2-yl) substituted pyrimidines from the commercially available 5-bromopyrimidine. The S-N(H) (AE)- and S-N(H) (AO)-reactions of 5-bromopyrimidine with thiophene and 2-bromothiophene have been studied by gas-liquid chromatography/mass-spectrometry. The structures of intermediate sigma(H)-adducts, as well as thiophene-(thiophenyl)pyrimidine and bithiophene-(thiophenyl)pyrimidine dyads have first been established by X-ray crystallography analysis. (c) 2012 Elsevier Ltd. All rights reserved.

Author keywords:

Suzuki-Miyaura reaction; Nucleophilic aromatic substitution of hydrogen; Pyrimidines; Thiophenes; Microwave-assisted synthesis MOLECULAR-SCALE WIRES; PROTONATED 1,3-DIAZINES; COORDINATION ARRAYS; METAL; DERIVATIVES

DOI:

10.1016/j.tet.2012.04.095

Web of Science ID:

ISI:000306350800016

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 8
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	MOLECULAR-SCALE WIRES; PROTONATED 1,3-DIAZINES; COORDINATION ARRAYS; METAL; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	verbitsky@ios.uran.ru
Funding-Acknowledgement	Ural Division of the Russian Academy of Sciences (Program of Support of Young Scientists and Post-Graduates) {[}11-3-NP-627, 12-P-3-1014, 12-T-3-1025, 12-T-3-1031]; State Program for Supporting of Leading Scientific Schools of the Russian Federation {[}5505.2012.3]; Russian Foundation for Basic Research {[}10-03-96078-r\_ural\_a]
Funding-Text	This work was supported by the Ural Division of the Russian Academy of Sciences (Program of Support of Young Scientists and Post-Graduates No. 11-3-NP-627; Grants 12-P-3-1014, 12-T-3-1025 and 12-T-3-1031), the State Program for Supporting of Leading Scientific Schools of the Russian Federation (grant NSh 5505.2012.3) and the Russian Foundation for Basic Research (grant No. 10-03-96078-r\_ural\_a). The authors would like to thank Ms. Rashida K. Novikova for obtaining of the single-crystal X-ray diffraction data.
Number-of-Cited-References	30
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	25
Journal-ISO	Tetrahedron
Doc-Delivery-Number	973HM