Synthesis of Thiophene Analogues of the Tacrine Series (original) (raw)
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3-Amino-2-thiophenecarboxamides (3a-e) were synthesized from 2-(4-oxo-3-phenylthiazolidin-2-ylidene)malononitrile(1) and employed in the synthesis of a variety of thiophene derivatives. These 3-Amino-2-thiophenecarboxamides (3a-c) which when treated with aromatic aldehydes under relatively mild conditions produced the 3-arylideneamines (6a-d). Treatment of the carboxamide(3d) with triethylorthoformate gave the thiophene-3-ylformimidate (7). Reacting 3-aminothiophene-2-carboxamides (3b,c) with chloroacetyl chloride furnished 5-(2-chloro-N-phenylacetamido)-3-(2-chloroacetamido)-2carboxamides (8a,b). The 3-amino-2-thiophene carboxamides (3a-e) on reacting with acetic anhydride yielded the thienooxazinone(11). Ethyl 4-cyano-3-[(ethoxymethylene)amino]-5-phenylaminothiophene-2-carboxylate (12) when treated with hydrazine, phenylhydrazine and hydroxylamine yielded some interesting unexpected thiophene derivatives (13), (14) and (15).
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ARKIVOC: archive for organic chemistry
New 2-aminoselenophene-3-carbonitriles and 5-amino-1,3-thiazole-4-carbonitriles were made and reacted with cycloalkanones to give tetrahydroselenolo[2,3-b]quinolines, cycloalkene-fused selenolo[3,2-e]pyridines, [1,3]thiazolo[5,4-b]quinolines, thiazolo[4,5-e]pyridines and tetrahydro-[1,3]thiazolo[5,4-b]quinolines.
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A facile and convenient synthesis of bis(2-(1H-benzo[d]imidazol-2(3H)ylidene)-3-oxopropanenitrile), bis((3-amino-5-(methylthio)-1H-pyrazol-4-yl)methanone) and bis(2-thioxo-1,2-dihydropyrimidine-5-carbonitrile) derivatives incorporating a thieno-[2,3-b]thiophene moiety via versatile, readily accessible diethyl 3,4-dimethylthieno-[2,3b]thiophene-2,5-dicarboxylate (1) is described.