Studies on Heterocyclic Enaminonitriles. VII. : Reactions of 2-Amino-3-cyano-4,5-dihydrothiophenes with Acetylenic Esters

doi:10.1248/CPB.34.396

Paper

Studies on Heterocyclic Enaminonitriles. VII. : Reactions of 2-Amino-3-cyano-4,5-dihydrothiophenes with Acetylenic Esters

Published Jan 25, 1986 · H. Matsunaga, Miki Sonoda, Y. Tomioka

Chemical & Pharmaceutical Bulletin

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Abstract

The reactions of 2-amino-3-cyano-4, 5-dihydrothiophene (Ia) and 2-amino-3-cyano-5-methyl-(or 4-phenyl)-4, 5-dihydrothiophene (Ib or Ic) with dimethyl acetylenedicarboxylate (DMAD) or methyl propiolate in dimethyl sulfoxide (DMSO) or hexamethylphosphoric triamide gave the corresponding dimethyl(or methyl) 2-amino-5-cyano-6, 7-dihydrothiepin-3, 4-dicarboxylate(or 3-carboxylate) (IIa-c or IVa-c). Compounds Ia-c reacted with DMAD in refluxing xylene to give the corresponding dimethyl α-(3-cyano-4, 5-dihydro-2-thienylamino)fumarates (IIIa-c).

Study Snapshot

Dimethyl acetylenedicarboxylate and methyl propiolate can produce dimethyl 2-amino-5-cyano-6, 7-dihydrothiepin-3, 4-dicarboxylate, which can be further converted into dimethyl -(3-cyano-4, 5-

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Studies on Heterocyclic Enaminonitriles. VII. : Reactions of 2-Amino-3-cyano-4,5-dihydrothiophenes with Acetylenic Esters

References

Citations

Synthesis of sulfur-containing heterocycles via ring enlargement

Ring expansion reactions are a convenient method for synthesizing medium-sized sulfur heterocycles, offering superior atomic and conversion efficiency compared to alternative classical iterative synthetic approaches.

Synthesis of Dihydrooxepins by the Cycloaddition of 2-Amino-4,5-dihydro-3-furancarbonitriles with Dimethyl Acetylenedicarboxylate.

This study presents a facile and efficient synthesis of dihydrooxepins by cycloaddition of readily available 2-amino-4,5-dihydro-3-furancarbonitriles with dimethyl acetylenedicarboxylate at room temperature.

Concise synthesis of fused polycyclic quinolines

This study presents a method for synthesizing fused polycyclic quinolines by domino [2+2] cycloaddition/annelation reaction with ynones and cyclic ketones.

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The Diels-Alder reaction of 5-aminopyrazole-4-carbonitrile with dimethyl acetylenedi-carboxylate produces dimethyl 2-(p-toluenesulfonylamino)-3-cyano-4-imino-1,4