C(sp3)-H functionalization of methyl azaarenes: a calcium-catalyzed facile synthesis of (E)-2-styryl azaarenes and 2-aryl-1,3-bisazaarenes

Srinivasarao Yaragorla, Garima Singh, Ravikrishna Dada

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

Alkaline earth (Ca2+) catalyzed sp3 C-H functionalization of methyl azaarenes for the synthesis of biologically important (E)-2-styryl azaarenes, 2-aryl-1,3-bisazaarenes and 3,3-bisazaarenyl indolinones has been described. Initially methyl azaarenes react with aryl aldehydes to give β-hydroxy derivatives, which undergo Ca(II) catalyzed thermodynamic elimination to give the styryl azaarenes in a single step. Similarly it may undergo SN1 reaction to give 2-aryl-1,3-bisazaarenes and 3,3-bisazaarenyl indolinones (if isatin used as the electrophile). This green synthetic methodology enjoys the simple reaction procedures, solvent free conditions, step economy, substrate diversity and high yields of the products in short time.

Original languageEnglish (US)
Pages (from-to)5924-5929
Number of pages6
JournalTetrahedron Letters
Volume56
Issue number43
DOIs
StatePublished - Oct 21 2015
Externally publishedYes

Bibliographical note

Funding Information:
S.Y. acknowledges DST -India, for their financial support. G.S. and R.D. thank Central University of Rajasthan and CSIR – India for their fellowships respectively.

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

  • Ca(II) catalysis
  • Heterocyclic compounds
  • Multicomponent reactions
  • Solvent free synthesis
  • sp C-H functionalization
  • Styryl azaarenes

Fingerprint

Dive into the research topics of 'C(sp3)-H functionalization of methyl azaarenes: a calcium-catalyzed facile synthesis of (E)-2-styryl azaarenes and 2-aryl-1,3-bisazaarenes'. Together they form a unique fingerprint.

Cite this