Conjugate additions of lithium dialkynylcuprates [(RC≡C)2CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system

Dan E. Daia; Christopher D. Gabbutt; B. Mark Heron; John D. Hepworth; Michael B. Hursthouse; K. M.Abdul Malik

doi:10.1016/S0040-4039(02)02857-5

Conjugate additions of lithium dialkynylcuprates [(RC≡C)₂CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system

Dan E. Daia, Christopher D. Gabbutt, B. Mark Heron, John D. Hepworth, Michael B. Hursthouse, K. M.Abdul Malik

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

25 Citations (Scopus)

Abstract

Lithium dialkynylcuprates [(RC≡C)₂CuLi], 1a-d, are easily generated and undergo conjugate additions to activated chromones giving 2-alkynylchroman-4-ones 4a-d, 13, 15c,d and 5, however, 1,4-additions to 3 proceed anomalously to give the eneynonitriles 6a-b and the bisbenzopyranopyridine 7.

Original language	English
Pages (from-to)	1461-1464
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	7
Early online date	30 Jan 2003
DOIs	https://doi.org/10.1016/S0040-4039(02)02857-5
Publication status	Published - 10 Feb 2003
Externally published	Yes

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title = "Conjugate additions of lithium dialkynylcuprates [(RC≡C)2CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system",

abstract = "Lithium dialkynylcuprates [(RC≡C)2CuLi], 1a-d, are easily generated and undergo conjugate additions to activated chromones giving 2-alkynylchroman-4-ones 4a-d, 13, 15c,d and 5, however, 1,4-additions to 3 proceed anomalously to give the eneynonitriles 6a-b and the bisbenzopyranopyridine 7.",

author = "Daia, \{Dan E.\} and Gabbutt, \{Christopher D.\} and Heron, \{B. Mark\} and Hepworth, \{John D.\} and Hursthouse, \{Michael B.\} and Malik, \{K. M.Abdul\}",

year = "2003",

month = feb,

day = "10",

doi = "10.1016/S0040-4039(02)02857-5",

language = "English",

volume = "44",

pages = "1461--1464",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "7",

}

Conjugate additions of lithium dialkynylcuprates [(RC≡C)₂CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system. / Daia, Dan E.; Gabbutt, Christopher D.; Heron, B. Mark et al.
In: Tetrahedron Letters, Vol. 44, No. 7, 10.02.2003, p. 1461-1464.

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

TY - JOUR

T1 - Conjugate additions of lithium dialkynylcuprates [(RC≡C)2CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system

AU - Daia, Dan E.

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Hepworth, John D.

AU - Hursthouse, Michael B.

AU - Malik, K. M.Abdul

PY - 2003/2/10

Y1 - 2003/2/10

N2 - Lithium dialkynylcuprates [(RC≡C)2CuLi], 1a-d, are easily generated and undergo conjugate additions to activated chromones giving 2-alkynylchroman-4-ones 4a-d, 13, 15c,d and 5, however, 1,4-additions to 3 proceed anomalously to give the eneynonitriles 6a-b and the bisbenzopyranopyridine 7.

AB - Lithium dialkynylcuprates [(RC≡C)2CuLi], 1a-d, are easily generated and undergo conjugate additions to activated chromones giving 2-alkynylchroman-4-ones 4a-d, 13, 15c,d and 5, however, 1,4-additions to 3 proceed anomalously to give the eneynonitriles 6a-b and the bisbenzopyranopyridine 7.

UR - https://www.scopus.com/pages/publications/0037429097

U2 - 10.1016/S0040-4039(02)02857-5

DO - 10.1016/S0040-4039(02)02857-5

M3 - Article

AN - SCOPUS:0037429097

SN - 0040-4039

VL - 44

SP - 1461

EP - 1464

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Conjugate additions of lithium dialkynylcuprates [(RC≡C)₂CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system

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