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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Notes

  1. *Here and henceforward, the numbering of the atoms was selected for convenience in discussion of the NMR spectra and does not correspond to the IUPAC nomenclature numbering.

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Authors and Affiliations

  1. St. Petersburg State University, 26 Universitetskiy Pr., 198504, St. Petersburg, Russia

    N. A. Danilkina & L. E. Mikhaylov

  2. St. Petersburg State Chemical-Pharmaceutical Academy, 14 Prof. Popova St., St. Petersburg, 197022, Russia

    B. A. Ivin

Authors
  1. N. A. Danilkina
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  2. L. E. Mikhaylov
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  3. B. A. Ivin
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Correspondence to N. A. Danilkina or B. A. Ivin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1079–1095, July, 2011.

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Danilkina, N.A., Mikhaylov, L.E. & Ivin, B.A. 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. Chem Heterocycl Comp 47, 886–900 (2011). https://doi.org/10.1007/s10593-011-0850-9

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