A simple synthesis of the pentacyclic lamellarin skeleton from 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1-methyl(benzyl)-3,4-dihydroisoquinolines / Korotaev Vladislav Yu.,Sosnovskikh Vyacheslav Ya.,Barkov Alexey Yu.,Slepukhin Pavel A.,Ezhikova Marina A.,Kodess Mikhail I.,Shklyaev Yurii V. // TETRAHEDRON. - 2011. - V. 67, l. 45. - P. 8685-8698.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

The basic structural framework of lamellarin alkaloids, 8,9-dihydro-6H-chromenc{[}4',3':4,5]pyrrolo{[}2,1-a] isoquinoline derivatives, has been obtained in good yields via Grob synthesis between 3-nitro-2-(trifluoromethyl)-2H-chromenes and 1-methyl-3,4-dihydroisoquinolines in refluxing isobutanol. In the case of 1-benzyl-3,4-dihydroisoquinolines, a dynamic NMR effect was observed in the H-1 and F-19 NMR spectra of the products as a result of restricted rotation about the single bond linking a e benzene ring and the heterocyclic system. When the reaction was carried out with 3-nitro-2-(trichloro methyl)-2H-chromenes in toluene at room temperature, only Michael adducts, as a mixture of two diastereomers, were isolated. (C) 2011 Elsevier Ltd. All rights reserved.

Author keywords:

Lamellarin skeleton; Grob reaction; 3-Nitro-2-(trifluoromethyl)-2H-chromenes; 3,4-Dihydroisoquinolines 3+2 CYCLOADDITION REACTIONS; ASCIDIAN DIDEMNUM-OBSCURUM; SUBSTITUTED PTEROCARPANS; MICHAEL-ADDITION; POLYFLUOROCARBONYL COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES

DOI:

10.1016/j.tet.2011.09.049

Web of Science ID:

ISI:000296407000014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 11
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	3+2 CYCLOADDITION REACTIONS; ASCIDIAN DIDEMNUM-OBSCURUM; SUBSTITUTED PTEROCARPANS; MICHAEL-ADDITION; POLYFLUOROCARBONYL COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	sosn1951@mail.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}11-03-00126]; RAS {[}N 21]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (Grant 11-03-00126) and the Presidium program of the RAS N 21.
Number-of-Cited-References	63
Usage-Count-Since-2013	18
Journal-ISO	Tetrahedron
Doc-Delivery-Number	839ZC