Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes.

Jury J Medvedev, Ilya V Efimov, Yuri M Shafran, Vitaliy V Suslonov, Vasiliy A Bakulev, Valerij A Nikolaev

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Article in Beilstein journal of organic chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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6 authors.

Jury J MedvedevDepartment of Organic Chemistry, St-Petersburg State University, 26 University pr., 198504, Saint-Petersburg, Russia.ORCID 0000-0002-4156-7455

Ilya V EfimovInstitute of Chemistry and Technology, Ural Federal University, 19 Mira Str., 620002, Ekaterinburg, Russia.ORCID 0000-0003-1123-987X

Yuri M ShafranInstitute of Chemistry and Technology, Ural Federal University, 19 Mira Str., 620002, Ekaterinburg, Russia.ORCID 0000-0001-5745-7624

Vitaliy V SuslonovCenter for X-ray Diffraction Studies, St-Petersburg State University, 26 University pr., 198504, Saint-Petersburg, Russia.ORCID 0000-0002-0769-3992

Vasiliy A BakulevInstitute of Chemistry and Technology, Ural Federal University, 19 Mira Str., 620002, Ekaterinburg, Russia.ORCID 0000-0001-9448-1447

Valerij A NikolaevDepartment of Organic Chemistry, St-Petersburg State University, 26 University pr., 198504, Saint-Petersburg, Russia.ORCID 0000-0001-5517-484X

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6 · The paper itself

Abstract

A new approach towards the synthesis of multisubstituted thiophenes is elaborated based on Rh(II)-catalyzed domino reactions of acyclic diazoesters with α-cyanothioacetamides. It provides a way for the preparation of 5-amino-3-(alkoxycarbonylamino)thiophene-2-carboxylates, 2-(5-amino-2-methoxycarbonylthiophene-3-yl)aminomalonates and (2-cyano-5-aminothiophene-3-yl)carbamates with the preparative yields of up to 67%. It was also shown that α-cyanothioacetamides easily interact with dirhodium carboxylates to give rather stable 2:1 complexes, resulting in an evident decrease in the efficiency of the catalytic process at moderate temperatures (20-30 °C).

Indexed as

[4 + 1]-annulationcatalysisdiazo compoundsdomino reactionsthiophenes

Identifiers

PMID29259666

DOI10.3762/bjoc.13.253

PMCPMC5727864

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