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Synthesis 2018; 50(24): 4982-4988
DOI: 10.1055/s-0037-1610239
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 1-Carboxamide-1,4-dihydropyridazines via Recycli­zation of Hydroxypyrrolines with Semicarbazides

Dmitrii A. Shabalin
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Evgeniya E. Ivanova
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Anton V. Kuzmin
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
b   Limnological Institute, Siberian Branch of the Russian Academy of Sciences, 3 Ulan-Batorskaya St, Irkutsk 664033, Russian Federation
,
Marina Yu. Dvorko
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Elena Yu. Schmidt
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
,
Boris A. Trofimov*
a   A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author AffiliationsThe reported study was funded by RFBR according to the research project No. 18-33-00089. The spectral data were obtained with the equipment of the Baikal Analytical Center for collective use SB RAS.
Further Information

Publication History

Received: 28 May 2018

Accepted after revision: 19 July 2018

Publication Date:
22 August 2018 (online)

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Abstract

Recyclization of available 5-hydroxypyrrolines with semicarbazide and its analogues has been studied. As a result, rare 1,4-dihydropyridazines with carboxamide function at the N-1 atom have been synthesized in up to 88% isolated yields.

Key words

dihydropyridazine - semicarbazide - hydroxypyrroline - carboxamide - DFT studies

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610239.
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