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Furochromone-isatin conjugates via an uncatalyzed diastereoselective [4 + 1] cycloaddition/tautomerization/Friedel-Crafts hydroxyalkylation domino reaction.

Authors :
Teimouri, Mohammad Bagher
Zolfaghari, Fatemeh
Naderi, Soheila
Source :
Tetrahedron. Jan2017, Vol. 73 Issue 3, p262-271. 10p.
Publication Year :
2017

Abstract

A series of diverse polycyclic heterocycles containing 3-hydroxyoxindole, and alkyliminofurochromone fused rings have been synthesized through the uncatalyzed Friedel-Crafts hydroxyalkylation of 3-(alkylamino)-9 H -furo [3,4-b]chromen-9-ones generated in situ by the [4 + 1] cycloaddition/tautomerization of alkyl isocyanides and 3-formylchromones with isatin derivatives. The method is simple and provides a new class of pharmacologically important furochromone-isatin conjugates in moderate to good yields. The products bearing two contiguous stereogenic centers and one stereogenic group were obtained in excellent diastereoselectivities. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00404020
Volume :
73
Issue :
3
Database :
Academic Search Index
Journal :
Tetrahedron
Publication Type :
Academic Journal
Accession number :
120320349
Full Text :
https://doi.org/10.1016/j.tet.2016.12.010