Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters

Standard

Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters : A new entry for the synthesis of multisubstituted thiophenes. / Medvedev, Jury J.; Efimov, Ilya V.; Shafran, Yuri M.; Suslonov, Vitaliy V.; Bakulev, Vasiliy A.; Nikolaev, Valerij A.

In: Beilstein Journal of Organic Chemistry, Vol. 13, 30.11.2017, p. 2569-2576.

Research output: Contribution to journal › Article › peer-review

Author

Medvedev, Jury J. ; Efimov, Ilya V. ; Shafran, Yuri M. ; Suslonov, Vitaliy V. ; Bakulev, Vasiliy A. ; Nikolaev, Valerij A. / Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters : A new entry for the synthesis of multisubstituted thiophenes. In: Beilstein Journal of Organic Chemistry. 2017 ; Vol. 13. pp. 2569-2576.

BibTeX

@article{55aaf08873f14042b66bfbfba94f850e,

title = "Rh(II)-mediated domino [4 + 1]-annulation of α-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 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).",

keywords = "Catalysis, Diazo compounds, Domino reactions, Thiophenes, [4 + 1]-annulation",

author = "Medvedev, {Jury J.} and Efimov, {Ilya V.} and Shafran, {Yuri M.} and Suslonov, {Vitaliy V.} and Bakulev, {Vasiliy A.} and Nikolaev, {Valerij A.}",

note = "Publisher Copyright: {\textcopyright} 2017 Medvedev et al.; licensee Beilstein-Institut.",

year = "2017",

month = nov,

day = "30",

doi = "10.3762/bjoc.13.253",

language = "English",

volume = "13",

pages = "2569--2576",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters

T2 - A new entry for the synthesis of multisubstituted thiophenes

AU - Medvedev, Jury J.

AU - Efimov, Ilya V.

AU - Shafran, Yuri M.

AU - Suslonov, Vitaliy V.

AU - Bakulev, Vasiliy A.

AU - Nikolaev, Valerij A.

PY - 2017/11/30

Y1 - 2017/11/30

N2 - 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).

AB - 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).

KW - Catalysis

KW - Diazo compounds

KW - Domino reactions

KW - Thiophenes

KW - [4 + 1]-annulation

UR - http://www.scopus.com/inward/record.url?scp=85040463064&partnerID=8YFLogxK

U2 - 10.3762/bjoc.13.253

DO - 10.3762/bjoc.13.253

M3 - Article

AN - SCOPUS:85040463064

VL - 13

SP - 2569

EP - 2576

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 87281451