REACTIONS OF N-CHLOROMETHYL-2-THIONOBENZOXAZOLES AND BENZOTHIAZOLES SYNTHESIS OF S-TRIAZOLO- AND 1,2,4-OXADIAZOLO FUSED SYSTEMS
N-chloromethyl-2-thiono-benzoxazole 1 and benzothiazole 2 undergo nucleophilic substitution by sulfur, oxygen and nitrogen nucleophiles.Condensation of compounds 1 and 2 with hydrazine, phenylhydrazine and hydroxylamine afforded the s-triazolo- and 1,2,4-
Abdel-Rahman, M. A.,Ghattas, A.-B. A. G.,El-Saraf, G. A.,Khodary, A.
p. 183 - 192
(2007/10/02)
Synthesis of 2-Thioxo-3-benzothiazolineacetonitrile and Related Products
Attempts to thermally rearrange 2-benzothiazolylthioacetonitrile (1) to the titled compound 8 failed.The reaction of 3-chloromethyl-2-benzothiazolinethione with potassium cyanide in dimethylformamide (DMF) or dimethylsulfoxide (DMSO) at 25-30 deg C afforded 8 in 98percent yield.Whereas replacing the DMF or DMSO solvent with acetone furnished the unexpected sulfide 9 in 92percent yield.Substituting 3-chloromethyl-2-benzoxazolinethione as the electrophile in the same reaction gave the sulfide 10 in 95percent yield.Possible mechanisms and supporting nmr data are discussed.
D'Amico, John J.,Suba, Lydia,Ruminski, Peter G.
p. 1479 - 1482
(2007/10/02)
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