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Interaction of 7-Chloro-9-methylthio-3-phenylpyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine with Some Nucleophiles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reactions of 7-chloro-9-methylthio-3-phenylpyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine (1) with some nucleophiles have been studied. Substitution of the chlorine atom with hydrogen occurs with ammonia in DMSO to give 9-methylthio-3-phenylpyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-7(8H)-one. With a methanolic solution of ammonia the 7-methoxy derivative is formed. Reaction of compound 1 with an excess of sodium methoxide in methanol gave 6,7-dimethoxy-9-methylthio-3-phenyl-5,6-dihydropyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine. The corresponding 7-substituted derivatives were obtained when compound 1 was heated with morpholine or 2-(dimethylamino)ethylamine. The azomethine bond of the thiadiazepine ring is reduced by sodium borohydride to give the corresponding 5,6-dihydro derivatives.

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  1. Vilnius University, Vilnius, 2006, Lithuania

    A. Brukstus, I. Susvilo & S. Tumkevicius

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  1. A. Brukstus
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  2. I. Susvilo
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  3. S. Tumkevicius
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Brukstus, A., Susvilo, I. & Tumkevicius, S. Interaction of 7-Chloro-9-methylthio-3-phenylpyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine with Some Nucleophiles. Chemistry of Heterocyclic Compounds 39, 1079–1083 (2003). https://doi.org/10.1023/B:COHC.0000003528.86697.4c

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  • DOI: https://doi.org/10.1023/B:COHC.0000003528.86697.4c

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