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 language | English (US) |
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Pages (from-to) | 5924-5929 |
Number of pages | 6 |
Journal | Tetrahedron Letters |
Volume | 56 |
Issue number | 43 |
DOIs | |
State | Published - Oct 21 2015 |
Externally published | Yes |
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