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Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition. / Sakharov, Pavel A.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

In: Tetrahedron, Vol. 73, No. 31, 2017, p. 4663-4670.

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

Harvard

Sakharov, PA, Rostovskii, NV, Khlebnikov, AF & Novikov, MS 2017, 'Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition', Tetrahedron, vol. 73, no. 31, pp. 4663-4670. https://doi.org/10.1016/j.tet.2017.06.037

APA

Sakharov, P. A., Rostovskii, N. V., Khlebnikov, A. F., & Novikov, M. S. (2017). Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition. Tetrahedron, 73(31), 4663-4670. https://doi.org/10.1016/j.tet.2017.06.037

Vancouver

Sakharov PA, Rostovskii NV, Khlebnikov AF, Novikov MS. Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition. Tetrahedron. 2017;73(31):4663-4670. https://doi.org/10.1016/j.tet.2017.06.037

Author

Sakharov, Pavel A. ; Rostovskii, Nikolai V. ; Khlebnikov, Alexander F. ; Novikov, Mikhail S. / Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition. In: Tetrahedron. 2017 ; Vol. 73, No. 31. pp. 4663-4670.

BibTeX

@article{321b903b720a4a9881f73e4024ce2f96,
title = "Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition",
abstract = "A copper(I)-NHC-catalyzed annulation of 5-membered cyclic enols of furan, thiophene and indene family with 3-aryl-2H-azirines has been developed to provide a rapid access to furo[3,4-b]pyrrole, thieno[3,4-b]pyrrole, indeno[1,2-b]pyrrole derivatives. The reaction proceeds via a copper-initiated N–C2 azirine bond cleavage with the retention of the C[dbnd]N double bond in the annulation product. The reaction of tetronic acids with 3-aryl-2H-azirines can also proceed under catalyst-free conditions, through a double addition of the enol to the azirine, but this route provides poor yields of the annulation products. This is the first example of the N–C2 bond cleavage in 2-unsubstituted 2H-azirines in the absence of a transition metal catalyst.",
keywords = "Azirines, Copper catalysis, Enols, Synthetic methods",
author = "Sakharov, {Pavel A.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",
year = "2017",
doi = "10.1016/j.tet.2017.06.037",
language = "English",
volume = "73",
pages = "4663--4670",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "31",

}

RIS

TY - JOUR

T1 - Annulation of five-membered cyclic enols with 3-aryl-2H-azirines Catalytic versus non-catalytic cycloaddition

AU - Sakharov, Pavel A.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2017

Y1 - 2017

N2 - A copper(I)-NHC-catalyzed annulation of 5-membered cyclic enols of furan, thiophene and indene family with 3-aryl-2H-azirines has been developed to provide a rapid access to furo[3,4-b]pyrrole, thieno[3,4-b]pyrrole, indeno[1,2-b]pyrrole derivatives. The reaction proceeds via a copper-initiated N–C2 azirine bond cleavage with the retention of the C[dbnd]N double bond in the annulation product. The reaction of tetronic acids with 3-aryl-2H-azirines can also proceed under catalyst-free conditions, through a double addition of the enol to the azirine, but this route provides poor yields of the annulation products. This is the first example of the N–C2 bond cleavage in 2-unsubstituted 2H-azirines in the absence of a transition metal catalyst.

AB - A copper(I)-NHC-catalyzed annulation of 5-membered cyclic enols of furan, thiophene and indene family with 3-aryl-2H-azirines has been developed to provide a rapid access to furo[3,4-b]pyrrole, thieno[3,4-b]pyrrole, indeno[1,2-b]pyrrole derivatives. The reaction proceeds via a copper-initiated N–C2 azirine bond cleavage with the retention of the C[dbnd]N double bond in the annulation product. The reaction of tetronic acids with 3-aryl-2H-azirines can also proceed under catalyst-free conditions, through a double addition of the enol to the azirine, but this route provides poor yields of the annulation products. This is the first example of the N–C2 bond cleavage in 2-unsubstituted 2H-azirines in the absence of a transition metal catalyst.

KW - Azirines

KW - Copper catalysis

KW - Enols

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=85021700549&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.06.037

DO - 10.1016/j.tet.2017.06.037

M3 - Article

AN - SCOPUS:85021700549

VL - 73

SP - 4663

EP - 4670

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 31

ER -

ID: 13392585