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1,3-Dipolar cycloaddition; Endo-Selectivity; Dispiro-bis-oxindoles; HOMO-LUMO interaction

An efficient, atom economical, one-pot synthesis of endo^'- selective (dispiro 3,2^¢-pyrrolidinyl) bisoxindole containing three contiguous chiral stereocenters with two contiguous quaternary spirostereo centers have been achieved by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of L-proline. One-pot, azomethine ylide cycloaddition with a dipolarophile without using any catalyst have also been achieved in good yields. This new methodology offers many advantages of catalyst-free, mild reaction conditions, shorter reaction time, environmental friendliness, regio- and stereoselective processes in higher yields

PANNEERSELVAM YUVARAJ¹ HUIDROM BIRKUMAR SINGH¹ ARUN PRASATH LINGAM KANDAPALAM² DEVARAJAN KATHIRVELAN³ SANKARANARAYANAN NAGARAJAN⁴

1. CSIR-North East Institute of Science and Technology, Branch Laboratory, Imphal, Manipur 795004, India
2. Department of Chemistry, Kamaraj College, Thoothukudi, Tamil Nadu 628003, India
3. Department of Chemistry, Indian Institute of Technology-Hyderabad, Kandi, Telangana 502285, India
4. Department of Chemistry, National Institute of Technology Manipur, Imphal 795004, India

Published

20 June 2020

Manuscript received

15 November 2019

Manuscript revised

6 January 2020

Accepted

9 January 2020