1,3,4,5-Tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides

Anjum Ahmed; Jonathan Clayden; Michael Rowley

doi:10.1055/s-1999-2977

1,3,4,5-Tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides

Anjum Ahmed, Jonathan Clayden^*, Michael Rowley

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

28 Citations (Scopus)

Abstract

On treatment with t-BuLi and DMPU, 1-naphthamides bearing N-allyl or N- prenyl substituents cyclise to give a mixture of products from which seven- membered lactams can be isolated in up to 73% yield - the first example of an organolithium-C=C cyclisation leading to a seven-membered ring.

Original language	English
Pages (from-to)	1954-1956
Number of pages	3
Journal	SYNLETT
Issue number	12
DOIs	https://doi.org/10.1055/s-1999-2977
Publication status	Published - 1999

Keywords

Amide
Azepin
Cyclization
Dearomatisation
Lithium

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title = "1,3,4,5-Tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides",

abstract = "On treatment with t-BuLi and DMPU, 1-naphthamides bearing N-allyl or N- prenyl substituents cyclise to give a mixture of products from which seven- membered lactams can be isolated in up to 73% yield - the first example of an organolithium-C=C cyclisation leading to a seven-membered ring.",

keywords = "Amide, Azepin, Cyclization, Dearomatisation, Lithium",

author = "Anjum Ahmed and Jonathan Clayden and Michael Rowley",

year = "1999",

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AU - Ahmed, Anjum

AU - Clayden, Jonathan

AU - Rowley, Michael

PY - 1999

Y1 - 1999

N2 - On treatment with t-BuLi and DMPU, 1-naphthamides bearing N-allyl or N- prenyl substituents cyclise to give a mixture of products from which seven- membered lactams can be isolated in up to 73% yield - the first example of an organolithium-C=C cyclisation leading to a seven-membered ring.

AB - On treatment with t-BuLi and DMPU, 1-naphthamides bearing N-allyl or N- prenyl substituents cyclise to give a mixture of products from which seven- membered lactams can be isolated in up to 73% yield - the first example of an organolithium-C=C cyclisation leading to a seven-membered ring.

KW - Amide

KW - Azepin

KW - Cyclization

KW - Dearomatisation

KW - Lithium

UR - http://www.scopus.com/inward/record.url?scp=0032740421&partnerID=8YFLogxK

U2 - 10.1055/s-1999-2977

DO - 10.1055/s-1999-2977

M3 - Article (Academic Journal)

AN - SCOPUS:0032740421

SN - 0936-5214

SP - 1954

EP - 1956

JO - SYNLETT

JF - SYNLETT

IS - 12

ER -

1,3,4,5-Tetrahydroazepin-2-ones by dearomatising anionic cyclisation of N-allyl-1-naphthamides

Abstract

Keywords

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