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Microwave‐Assisted One‐Pot [3+2] Cycloaddition of Azomethine Ylides and 3‐Alkenyl Oxindoles: A Facile Approach to Pyrrolidine‐Fused Bis‐Spirooxindoles
Author(s) -
Bhandari Sonal,
Sana Sravani,
Sridhar Balasubramanyam,
Shankaraiah Nagula
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201802847
Subject(s) - pyrrolidine , azomethine ylide , cycloaddition , chemistry , substrate (aquarium) , catalysis , ring (chemistry) , organic chemistry , combinatorial chemistry , polymer chemistry , 1,3 dipolar cycloaddition , oceanography , geology
An efficient microwave‐assisted one‐pot method has been developed for the construction of pyrrolidine fused bis‐spirooxindoles through insitu generated azomethine ylide from decarboxylative condensation of isatins and primary α‐amino acids with concomitant [3+2] cycloaddition of 3‐alkenyl oxindoles. These reactions were effectively accelerated by microwave irradiation in ethanol solvent without any additives or catalyst and enable broad substrate scope, atom‐economy, eco‐friendly, and good yields. The structure and stereochemistry of pyrrolidine fused bis‐spirooxindole ring was unambiguously established by single‐crystal X‐ray analysis.