One pot synthesis of novel dispiro[oxindole‐thiazolidinedione/thioxo‐thiazolidinone/dihydro pyrazolone]‐pyrrolidines via 1,3‐dipolar cycloaddition reaction of azomethine ylides | Zendy

Ponnala Shashikanth | Zendy; Sahu Devi Prasad | Zendy; Kumar Rishi | Zendy; Maulik Prakas R. | Zendy

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One pot synthesis of novel dispiro[oxindole‐thiazolidinedione/thioxo‐thiazolidinone/dihydro pyrazolone]‐pyrrolidines via 1,3‐dipolar cycloaddition reaction of azomethine ylides

Author(s) -

Ponnala Shashikanth,

Sahu Devi Prasad,

Kumar Rishi,

Maulik Prakas R.

Publication year - 2006

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.5570430631

Subject(s) - chemistry , oxindole , azomethine ylide , pyrrolidine , pyrazolone , 1,3 dipolar cycloaddition , cycloaddition , pyrazolones , yield (engineering) , organic chemistry , stereochemistry , catalysis , materials science , metallurgy

A series of novel dispiro[oxindole‐thiazolidinedione]pyrrolidine, dispiro[oxindole‐thioxothiazolidinone]‐pyrrolidine, dispiro[oxindole‐dihydro‐pyrazolone]pyrrolidine were synthesized by both regio‐ and stereo‐selective 1,3‐dipolar cycloaddition reaction of azomethine ylide generated from amino acid and amino acid ester with π‐deficient alkenes in a single pot protocol in good yield. X‐ ray crystallographic studies established orthogonal disposition between spiro‐oxindole and spiro‐thiazolidinedione rings in 4a and 5a .

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