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

ABSTRACT: A new approach towards the synthesis of multisubstituted thiophenes is elaborated based on Rh(II)-catalyzed domino reactions of acyclic diazoesters with ?-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 ?-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).

SUBMITTER: Medvedev JJ

PROVIDER: S-EPMC5727864 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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

Medvedev Jury J JJ Efimov Ilya V IV Shafran Yuri M YM Suslonov Vitaliy V VV Bakulev Vasiliy A VA Nikolaev Valerij A VA

Beilstein journal of organic chemistry 20171130

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 carb ...[more]

PMID: 29259666

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