Chemistry of Heterocyclic Compounds

, Volume 47, Issue 7, pp 886–900 | Cite as

Reaction of acetylenedicarboxylic acids esters with 4,5-dihydro-1H-pyrazole-1-carbothioamides and 3,4,5,6-tetrahydro-2H-1,2,4-triazepine-3-thiones

  • N. A. DanilkinaEmail author
  • L. E. Mikhaylov
  • B. A. IvinEmail author

The reactions of dimethyl acetylenecarboxylate with 3,4,5,6-tetrahydro-2H-1,2,4-triazepine-3-thiones and 4,5-dihydro-1H-pyrazole-1-carbothioamides are convenient methods for the synthesis of 7,8-dihydrothiazolo[3,2-b][1,2,4]triazepin-3-ones derivatives and methyl esters of (2Z)-[2-(4,5-dihydro-1H-pyrazol-1-yl)-4-oxo-1,3-thiazol-5(4H)-ylidene]acetic acids, respectively. The reaction of methyl propynoates with 4,5-dihydro-1H-pyrazole-1-carbothioamides or with 5,5,7-trimethyl-2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thione gives 2-(4,5-dihydro-1H-pyrazol-1-yl)-4H-1,3-thiazin-4-ones.


4,5-dihydro-1H-pyrazole-1-carbothioamides 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones 1,3-thiazin-4-ones 1,3-thiazol-4-ones thiazolo[3,2-b][1,2,4]triazepin-3-ones acetylenecarboxylic acids esters C–H coupling constants 


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© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.St. Petersburg State Chemical-Pharmaceutical AcademySt. PetersburgRussia

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