Issue 7, 2012
From the journal:

RSC Advances

Catalyst-and solvent-free one-pot synthesis of some novel polyheterocycles from aryldiazenyl salicylaldehyde derivatives†

Narsidas J. Parmar,*a   Rikin A. Patel,a   Shashikant B. Teraiya,a   Deepak Sharmab  and  Vivek K. Guptab  

* Corresponding authors

a Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar-388120. Dist. Anand, Gujarat, India
E-mail: njpchemdeptspu@yahoo.co.in

b Post-Graduate Department of Physics, University of Jammu, Jammu Tawi-180 006, India

Abstract

A catalyst-and solvent-free domino/Knoevenagel-hetero-Diels–Alder (DKHDA) reaction of two aldyhyde substrates, allyl/prenyl ether tethered aryldiazenylsalicylaldehydes with corresponding pyrazolones and heterocyclic 1,3-diketones is described. Subsequent reduction of aryldiazenylpolyheterocycles, thus obtained in high yields (70–86%), afforded analogues amino frameworks with anticipated biological activity. While in a conventional procedure, no reaction was observed without activation of an allyl-based substrate, an excellent yield was achieved at higher temperature. For a prenyl based substrate, however it underwent smoothly to form a desired cyclised product. The stereochemistry of the compound was confirmed by various NMR experiments and a single crystal X-ray diffraction analysis.

Graphical abstract: Catalyst-and solvent-free one-pot synthesis of some novel polyheterocycles from aryldiazenyl salicylaldehyde derivatives

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Article information

DOI
https://doi.org/10.1039/C2RA00930G
Article type
Paper
Submitted
20 Oct 2011
Accepted
09 Jan 2012
First published
21 Feb 2012

RSC Adv., 2012,2, 3069-3075

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Catalyst-and solvent-free one-pot synthesis of some novel polyheterocycles from aryldiazenyl salicylaldehyde derivatives

N. J. Parmar, R. A. Patel, S. B. Teraiya, D. Sharma and V. K. Gupta, RSC Adv., 2012, 2, 3069 DOI: 10.1039/C2RA00930G

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