A one-pot synthesis of 4-aryl-2-methyl-1,2,3,4-tetrahydro-gamma-carbolines from 5-aryloxazolidines and indoles via a Mannich/Friedel-Crafts sequence / Moshkin Vladimir S.,Sosnovskikh Vyacheslav Y. // TETRAHEDRON LETTERS. - 2014. - V. 55, l. 44. - P. 6121-6124.

ISSN/EISSN:
0040-4039 / нет данных
Type:
Article
Abstract:
Benzaldehydes react smoothly with the nonstabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines, which undergo ring-opening to give 2-(indol-3-ylmethylamino)-1-arylethanols in 69-79\% yields on reaction with indoles in acetic acid. Their subsequent acid-catalyzed cyclization into 4-aryl-2-methyl-1,2,3,4-tetrahydro-gamma-carbolines was performed in polyphosphoric acid in moderate yields. The latter can also be prepared directly from 5-aryloxazolidines and indoles in polyphosphoric acid. (C) 2014 Elsevier Ltd. All rights reserved.
Author keywords:
5-Aryloxazolidines; Indoles; 1,2,3,4-Tetrahydro-gamma-carbolines; Phenylethanolamines; Benzaldehydes; Nonstabilized azomethine ylides GAMMA-CARBOLINES; DERIVATIVES; CYCLIZATION
DOI:
10.1016/j.tetlet.2014.09.058
Web of Science ID:
ISI:000343625300025
Соавторы в МНС:
Другие поля
Поле Значение
Month OCT 29
Publisher PERGAMON-ELSEVIER SCIENCE LTD
Address THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language English
Keywords-Plus GAMMA-CARBOLINES; DERIVATIVES; CYCLIZATION
Research-Areas Chemistry
Web-of-Science-Categories Chemistry, Organic
Author-Email mvslc@mail.ru
ResearcherID-Numbers Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement Russian Science Foundation {[}14-13-00388]; Ural Federal University development program
Funding-Text This work was financially supported by the Russian Science Foundation (Grant 14-13-00388) and carried out under the terms of the Ural Federal University development program with the financial support of young scientists.
Number-of-Cited-References 19
Usage-Count-Last-180-days 1
Usage-Count-Since-2013 16
Journal-ISO Tetrahedron Lett.
Doc-Delivery-Number AR5LD