Perilithiation and the synthesis of 8-substituted-1-naphthamides

Jonathan Clayden; Christopher S. Frampton; Catherine McCarthy; Neil Westlund

doi:10.1016/S0040-4020(99)00881-9

Perilithiation and the synthesis of 8-substituted-1-naphthamides

Jonathan Clayden^*
, Christopher S. Frampton
, Catherine McCarthy
, Neil Westlund

^*Corresponding author for this work

School of Chemistry

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

59 Citations (Scopus)

Abstract

Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing 1-substituents such as -NMe₂ or CH₂NMe₂ allows the synthesis of 8-substituted-1-naphthamldes. The 8- CH₂NMe₂ substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material.

Original language	English
Pages (from-to)	14161-14184
Number of pages	24
Journal	Tetrahedron
Volume	55
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4020(99)00881-9
Publication status	Published - 3 Dec 1999

Research Groups and Themes

Organic & Biological

Keywords

Amides
Lithiation
Naphthalenes
Polonoski reaction

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10.1016/S0040-4020(99)00881-9

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@article{f766ed40e09e4cbc84d40676566713cf,

title = "Perilithiation and the synthesis of 8-substituted-1-naphthamides",

abstract = "Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing 1-substituents such as -NMe2 or CH2NMe2 allows the synthesis of 8-substituted-1-naphthamldes. The 8- CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material.",

keywords = "Amides, Lithiation, Naphthalenes, Polonoski reaction",

author = "Jonathan Clayden and Frampton, \{Christopher S.\} and Catherine McCarthy and Neil Westlund",

year = "1999",

month = dec,

day = "3",

doi = "10.1016/S0040-4020(99)00881-9",

language = "English",

volume = "55",

pages = "14161--14184",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "49",

}

TY - JOUR

T1 - Perilithiation and the synthesis of 8-substituted-1-naphthamides

AU - Clayden, Jonathan

AU - Frampton, Christopher S.

AU - McCarthy, Catherine

AU - Westlund, Neil

PY - 1999/12/3

Y1 - 1999/12/3

N2 - Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing 1-substituents such as -NMe2 or CH2NMe2 allows the synthesis of 8-substituted-1-naphthamldes. The 8- CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material.

AB - Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing 1-substituents such as -NMe2 or CH2NMe2 allows the synthesis of 8-substituted-1-naphthamldes. The 8- CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material.

KW - Amides

KW - Lithiation

KW - Naphthalenes

KW - Polonoski reaction

UR - https://www.scopus.com/pages/publications/0033521051

U2 - 10.1016/S0040-4020(99)00881-9

DO - 10.1016/S0040-4020(99)00881-9

M3 - Article (Academic Journal)

AN - SCOPUS:0033521051

SN - 0040-4020

VL - 55

SP - 14161

EP - 14184

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

Perilithiation and the synthesis of 8-substituted-1-naphthamides

Abstract

Research Groups and Themes

Keywords

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