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

Conjugate additions of lithium dialkynylcuprates (RC C)(2)CuLi to activated chromones. Unexpected formation of the 6H-bis 1 benzopyrano 2,3-b : 3',4'-e pyridine system
Conjugate additions of lithium dialkynylcuprates (RC C)(2)CuLi to activated chromones. Unexpected formation of the 6H-bis 1 benzopyrano 2,3-b : 3',4'-e pyridine system
Lithium dialkynylcuprates [(RCequivalent toC)(2)CuLi], 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.
alpha, beta-unsaturated ketones, reagents, transmetalation, enones
0040-4039
1461-1464
Daia, D. E.
94edb3a4-cb4b-4cc8-b090-6f69620920a4
Gabbutt, C. D.
94192b7e-b99b-4611-943e-fe645f2d6a52
Heron, B. M.
64aef16b-7be8-40ee-980c-74f4169f8057
Hepworth, J. D.
8415acca-48d0-4964-83a5-acd903afd3d4
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Malik, K. M. A.
7aaa7d12-fc90-4954-8902-d12e4fbdccdd
Daia, D. E.
94edb3a4-cb4b-4cc8-b090-6f69620920a4
Gabbutt, C. D.
94192b7e-b99b-4611-943e-fe645f2d6a52
Heron, B. M.
64aef16b-7be8-40ee-980c-74f4169f8057
Hepworth, J. D.
8415acca-48d0-4964-83a5-acd903afd3d4
Hursthouse, M. B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Malik, K. M. A.
7aaa7d12-fc90-4954-8902-d12e4fbdccdd

Daia, D. E., Gabbutt, C. D., Heron, B. M., Hepworth, J. D., Hursthouse, M. B. and Malik, K. M. A. (2003) Conjugate additions of lithium dialkynylcuprates (RC C)(2)CuLi to activated chromones. Unexpected formation of the 6H-bis 1 benzopyrano 2,3-b : 3',4'-e pyridine system. Tetrahedron Letters, 44 (7), 1461-1464. (doi:10.1016/S0040-4039(02)02857-5).

Record type: Article

Abstract

Lithium dialkynylcuprates [(RCequivalent toC)(2)CuLi], 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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More information

Published date: 10 February 2003
Keywords: alpha, beta-unsaturated ketones, reagents, transmetalation, enones

Identifiers

Local EPrints ID: 19939
URI: https://eprints.soton.ac.uk/id/eprint/19939
ISSN: 0040-4039
PURE UUID: 8dd4f0ce-b7fa-4de0-82b8-99432247962b

Catalogue record

Date deposited: 17 Feb 2006
Last modified: 15 Jul 2019 19:26

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