MICROWAVE-MEDIATED InCl<sub>3</sub>-CATALYZED THREE-COMPONENT ANNELATION OF THIADIAZINЕ RING ON 4-AMINO-4<i>H</i>-[1,2,4]TRIAZOLE-3-THIOL

Authors

  • V. Srivastava Laboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad – 211002, U.P., India
  • P. K. Singh Food Analysis and Research Laboratory, Center of Food Technology, University of Allahabad, Allahabad – 211002, U.P., India
  • P. P. Singh United College of Engineering & Research, Naini, Allahabad - 211010

DOI:

https://doi.org/10.1007/1594

Keywords:

indium trichloride, triazolothiadiazine, annelation, microwave synthesis, three-component reaction

Abstract

A novel efficient three-component annelation of thiadiazinyl ring onto 4-amino-4H‑[1,2,4]triazole-3-thiol, catalyzed by non-toxic, recyclable InCl3 under microwave acti­va­tion has been developed. The transformation of 4-amino-5-aryl-4H-[1,2,4]triazole-3‑thiol into triazolothiadiazine involves chemoselective successive double addition reaction consisting of an InCl3-catalyzed dehydrative nucleophilic addition of amino group to an aromatic aldehyde followed by addition of the resulting Schiff's base to cyclohexyl isocyanide. The intramolecular cyclization of the adduct results in 3,6-diaryl-5H‑[1,2,4]­triazolo­[3,4‑b]­[1,3,4]thiadiazine. Reaction proceeds smoothly with good yields.

How to Cite
Srivastava, V.; Singh, P. K.; Singh, P. P. Chem. Heterocycl. Compd. 2014, 50, 573. [Khim. Geterotsikl. Soedin. 2014, 625.]

For this article in the English edition see DOI 10.1007/s10593-014-1509-0

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Published

2014-05-06

Issue

No. 4 (2014)

Section

Original Papers