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

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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.

в: Tetrahedron, Том 73, № 31, 2017, стр. 4663-4670.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

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