Browsing by Author "Jangale, A.D."

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    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
    (2015) 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.
    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.
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    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
    (American Chemical Society service@acs.org, 2015) 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.
    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.