Radical-based methodology for efficient generation of acyclic N-acylimines

被引：26

作者：

Chao, WC ^{[1
]}

Weinreb, SM ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 48期

基金：

美国国家卫生研究院;

关键词：

radicals and radical reactions; amides; nitrogen heterocycles; allylation; Diels-Alder reactions;

D O I：

10.1016/S0040-4039(00)01683-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha -Methoxybenzamides 11, which are convenient precursors of acyclic N-acylimines, can be cleanly generated in high yields via a free radical process starting from an o-aminobenzamide 16 derived from an N-t-butyl or N-cumyl secondary amine. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9199 / 9204

页数：6

共 21 条

[1] AlTalib M, 1996, SYNTHESIS-STUTTGART, P1115
[2] COMPETITION BETWEEN BOND ROTATIONS AND INTRAMOLECULAR HYDROGEN ATOM TRANSFER AS STUDIED BY USE OF ISOTOPE EFFECTS
COHEN, T
MCMULLEN, CH
SMITH, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) : 6866 - &
[3] COPPOLA GM, 1980, SYNTHESIS-STUTTGART, P505
[4] RADICAL TRANSLOCATION REACTIONS ACROSS AMIDES - 1,5-HYDROGEN-TRANSFER REACTIONS OF O-IODOBENZAMIDES AND N-(O-IODOBENZYL) AMIDES
CURRAN, DP
LIU, HT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (11): : 1377 - 1393
[5] Exploratory synthetic studies of the alpha-methoxylation of amides via cuprous ion-promoted decomposition of o-diazobenzamides
Han, G
LaPorte, MG
McIntosh, MC
Weinreb, SM
Parvez, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9483 - 9493
[6] HAN G, 1997, THESIS PENNSYLVANIA
[7] A CONVENIENT SYNTHETIC METHOD FOR AMIDE OXIDATION
HAN, GH
MCINTOSH, MC
WEINREB, SM
[J]. TETRAHEDRON LETTERS, 1994, 35 (32) : 5813 - 5816
[8] INTERNUCLEAR CYCLISATION .9. ABNORMAL REACTIONS OF 2-AMINO-N-METHYLBENZANILIDES CONTAINING ORTHO-SUBSITUENTS
HEY, DH
TURPIN, DG
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUL): : 2471 - 2481
[9] Hiemstra H., 1991, COMPREHENSIVE ORGANI, V2, P1047
[10] Hiemstra H., 1988, ALKALOIDS, V32, P271

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