The reaction of 3‐(dicyanomethylene)‐2‐indolone in a solution of ethanol/piperidine with 4‐substituted thiosemicarbazides forms the derivatives of 5′‐(substituted amino)‐3′H–spiro(indoline‐3,2′‐[1,3,4]thiadiazol‐2‐one. Rationales for these conversions involving the nucleophilic addition on the dicyanomethylene carbon atom are presented. The prepared compounds were evaluated each for antidepressant activity using tail suspension behavioral despair test and anticonvulsant activity against pentylenetetrazol induced seizures in mice. J. Heterocyclic Chem., (2011).
The Table of contents Title, author's name, address and table of contents S1 Crystallographic Data for Compound 5a S2-S7 Crystallographic Data for Compound 5c S8-S10 Table 10. Hydrogen-bond geometry (Å, º) of 5c
in Wiley Online Library (wileyonlinelibrary.com).New series of substituted aminothiadiazolylhydrazonoindolin-2-ones were prepared in high yields (89-94%) via the cyclocondensation of thiocarbonohydrazides (1a-d) with 3-(dicyanomethylene)-2-indolone in (ethanol/piperidine) at room temperature. Explanations of these conversations involve the nucleophilic addition on the dicyanomethylene carbon atom. The structures were established by spectroscopic data and single crystal X-ray crystallography.
A facile and rapid procedure for the synthesis of dimethyl-2-[3-amino-5-(2-methoxy-2-oxoethylidene)- 4-oxothiazolidin-2-ylidenehydrazono]succinate, dimethyl {[2-alkylidenehydrazono)-5-(2-methoxy- 2-oxoethylidene)-4-oxothiazolidin-3-yl)amino]succinate and methyl (4-amino-5-oxo-3- thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-yl)acetate affording yields of 61-54 %, 22-18 % and 14- 11 %, respectively, via a condensation reaction of dimethyl acetylenedicarboxylate (DMAD) with (substituted ylidene)thiocarbonohydrazides. One of the products was conclusively confirmed by single-crystal X-ray analysis. A mechanism for the formation of the products is presented.
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