Please use this identifier to cite or link to this item: https://idr.l1.nitk.ac.in/jspui/handle/123456789/11934
Title: Highly Efficient Regioselective Synthesis of 2-Imino-4-oxothiazolidin-5-ylidene Acetates via a Substitution-Dependent Cyclization Sequence under Catalyst-Free Conditions at Ambient Temperature
Authors: Wagh, Y.B.
Kuwar, A.S.
Patil, D.R.
Tayade, Y.A.
Jangale, A.D.
Terdale, S.S.
Trivedi, D.R.
Gallucci, J.
Dalal, D.S.
Issue Date: 2015
Citation: Industrial and Engineering Chemistry Research, 2015, Vol.54, 40, pp.9675-9682
Abstract: A green and efficient method for the synthesis of newer 2-imino-4-oxothiazolidin-5-ylidene acetate derivatives under catalyst-free conditions by simply stirring symmetrical and unsymmetrical 1,3-diarylthioureas with dialkyl acetylenedicarboxylates in ethanol at room temperature has been developed. Interestingly, the regioselective synthesis affords the 2-imino-4-oxothiazolidin-5-ylidene acetate derivatives: the amine nitrogen bonded to an electron-withdrawing substituent becomes part of the imino component, and the amine nitrogen bonded to an electron-donating substituent becomes the heterocyclic nitrogen. This is the first report wherein the impact of substituents in directing the regiocyclization has been explained and the structure conflict resolved by single-crystal X-ray analysis. 2015 American Chemical Society.
URI: http://idr.nitk.ac.in/jspui/handle/123456789/11934
Appears in Collections:1. Journal Articles

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