Consecutive SNH and Suzuki-Miyaura Cross-Coupling Reactions - an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments / Verbitskiy Egor V.,Rusinov Gennady L.,Charushin Valery N.,Chupakhin Oleg N.,Cheprakova Ekaterina M.,Slepukhin Pavel A.,Pervova Marina G.,Ezhikova Marina A.,Kodess Mikhail I. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2012. - V. , l. 33. - P. 6612-6621.

ISSN/EISSN:

1434-193X / нет данных

Type:

Article

Abstract:

The combination of the SuzukiMiyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)- and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The SNH {[}AE, (additionelimination)] and SNH {[}AO, (additionoxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatographymass spectrometry. The structures of the intermediate sH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis.

Author keywords:

Synthetic methods; Cross-coupling; Nucleophilic substitution; Nitrogen heterocycles; Microwave chemistry AROMATIC-SUBSTITUTION REACTIONS; NUCLEOPHILIC-SUBSTITUTION; PROTONATED 1,3-DIAZINES; HYDROGEN; DERIVATIVES; ARYL

DOI:

10.1002/ejoc.201201035

Web of Science ID:

ISI:000310981500016

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV
Publisher	WILEY-V C H VERLAG GMBH
Address	BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Language	English
Keywords-Plus	AROMATIC-SUBSTITUTION REACTIONS; NUCLEOPHILIC-SUBSTITUTION; PROTONATED 1,3-DIAZINES; HYDROGEN; DERIVATIVES; ARYL
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Verbitsky@ios.uran.ru
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}12-P-3-1014, 12-P-3-1030, 12-T-3-1025, 12-T-3-1031]; State Program for Supporting of Leading Scientific Schools of the Russian Federation {[}NSh 5505.2012.3]; Russian Foundation for Basic Research {[}10-03-96078-r\_ural\_a, 12-03-31574]
Funding-Text	This work was supported by the Ural Branch of the Russian Academy of Sciences (grants numbers 12-P-3-1014, 12-P-3-1030, 12-T-3-1025, and 12-T-3-1031), the State Program for Supporting of Leading Scientific Schools of the Russian Federation (grant number NSh 5505.2012.3), and the Russian Foundation for Basic Research (grant numbers 10-03-96078-r\_ural\_a and 12-03-31574).
Number-of-Cited-References	27
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	19
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	035WB