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Bis-MBH adduct; Oxindole; Nucleophilic substitution; Tri-substituted olefins; bis-pyrazole.

An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindole derivatives has been achieved from 3,5-bis-Morita-Baylis-Hillman (MBH) adducts of oxindole via nucleophilic substitution reaction for the first time. Wider scope of substrate and rate acceleration has been observed in second MBH reaction under typical reaction condition. The synthetic usefulness of bi-functionalized bis-allyl derivative has been demonstrated by the synthesis of potent bis-pyrazole via [3+2]-annulation strategy.

Kodirajan Selvakumar¹ Kandapalam Arun Prasath Lingam² Rama Varma Luxmi Varma³ Poovan Shanmugavelan⁴

1. Department of Chemistry, Thiagarajar College, Madurai 625 009, Tamil Nadu, India
2. Department of Chemistry, Kamaraj College, Tuticorin 628 003, Tamil Nadu, India
3. Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram 695 019, Kerala, India
4. Department of Chemistry, School of Science, Tamilnadu Open University, Saidapet, Chennai 600 015, Tamil Nadu, India

Published

August 2015

Manuscript received

27 November 2014

Manuscript revised

13 May 2015

Accepted

14 May 2015

• supp12.doc