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 journalArticle

21 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 languageEnglish
Pages (from-to)1461-1464
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number7
Early online date30 Jan 2003
DOIs
Publication statusPublished - 10 Feb 2003
Externally publishedYes

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Chromones
Lithium
pyridine

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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.",
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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; Hepworth, John D.; Hursthouse, Michael B.; Malik, K. M.Abdul.

In: Tetrahedron Letters, Vol. 44, No. 7, 10.02.2003, p. 1461-1464.

Research output: Contribution to journalArticle

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.

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

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

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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