铑（II）介导的重氮酯对α-氰基硫代乙酰胺的多米诺[4 + 1]环化反应：多取代噻吩合成的新方法。

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

作者信息

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

机构信息

Department of Organic Chemistry, St-Petersburg State University, 26 University pr., 198504, Saint-Petersburg, Russia.

Institute of Chemistry and Technology, Ural Federal University, 19 Mira Str., 620002, Ekaterinburg, Russia.

出版信息

Beilstein J Org Chem. 2017 Nov 30;13:2569-2576. doi: 10.3762/bjoc.13.253. eCollection 2017.

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).