A. Kalogirou, P. Koutentis, Maria D. Rikkou
Jun 17, 2010
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Abstract
abstract [3,5-Bis(dialkylamino)-4H-1,2,6-thiadiazin-4-ylidene]propanedinitriles 6a–c, react with sodium meth-oxide or ethoxide to give the corresponding 6-alkoxy-4-dialkylamino substituted pyrrolo[2,3-c][1,2,6]thiadiazine-5-carbonitriles 7a–f in variable yields. These new compounds are fully characterisedand two rational mechanisms are proposed for their formation. 2010 Elsevier Ltd. All rights reserved. 1. IntroductionVarious oxidised 1,2,6-thiadiazines such as the sulfoxides and,more importantly, the sulfones have received considerable atten-tion in various areas of applied chemistry including the pharma-ceutical, 1 agrochemical 2 and materials 3 sectors. Surprisingly little,however, has appeared in the literature on non-oxidised 4H-1,2,6-thiadiazines. Monocyclic 3,5-dichloro-4H-1,2,6-thiadiazin-4-one 1 4 and its 4-dicyanomethylene derivative 2 5,6 havebeenpreparedandboth are useful precursors to several polycyclic 1,2,6-thiadiazinesystems. 7 Furthermore, many mono-chloro derivatives of thiadia-zinone 1 have high fungicidal activity,