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One‐pot Regioselective Synthesis of Novel 1‐ N ‐Methyl‐spiro[2,3′]oxindole‐spiro[3,3″]‐1″‐ N ‐arylpyrrolidine‐2″,5″‐dione‐4‐arylpyrrolidines through Multicomponent 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylide
Author(s) -
Kaur Anjandeep,
Kaur Manpreet,
Singh Baldev
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2199
Subject(s) - regioselectivity , chemistry , oxindole , cycloaddition , azomethine ylide , sarcosine , pyrrolidine , isatin , ylide , selectivity , aryl , stereoselectivity , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , 1,3 dipolar cycloaddition , alkyl , catalysis , glycine , biochemistry , amino acid
An atom economic and facile synthesis of novel dispiro–oxindole–pyrrolidines has been achieved via a three‐component tandem cycloaddition of azomethine ylide generated in situ from isatin and sarcosine by decarboxylative condensation with N ‐aryl‐3‐benzylidene‐pyrrolidine‐2,5‐dione derivatives as dipolarophiles. The salient features of synthetic procedure are characterized by the mild reaction conditions, high yields, high regioselectivity and stereoselectivity, one‐pot procedure , and operational simplicity. This regioselectivity was assumed to be under the influence of π–π stacking interactions between the aromatic rings of azomethine ylide and N ‐aryl‐3‐benzylidene‐pyrrolidine‐2,5‐diones that further control the exo–endo selectivity of the reaction 1,3‐dipolar cycloaddition . The regiochemistry and structures of the cycloadducts were determined with spectroscopic data.