Intramolecular 1,6-Addition to 2-Pyridones. Mechanism and Synthetic Scope

被引：33

作者：

Gallagher, Timothy ^{[1
]}

Derrick, Ian ^{[2
]}

Durkin, Patrick M. ^{[1
]}

Haseler, Claire A. ^{[1
]}

Hirschhaeuser, Christoph ^{[1
]}

Magrone, Pietro ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] AstraZeneca, Proc Res & Dev, Avlon Works, Bristol BS10 7ZE, Avon, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

LITHIUM ALLYLDIBUTYLMAGNESATE; SMOKING-CESSATION; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/jo100514a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope and limitations of the intramolecular 1,6-addition of an enolate to a 2-pyridone moiety, a reaction that has found application in the synthesis of the lupin alkaloids, have been probed. This nucleophilic addition process has been shown to be reversible and favored in the case of (less stabilized) amide and lactam etiolates, which readily form five- and six-membered bi-/tricyclic products. Alternative etiolates (ketone, ester, thiolactam) and a variety of different acceptors (isoquinolinone, pyrimidinone, pyrazinone, pyridopyrazinone) have been evaluated, and a range of competing side reactions have been identified and characterized using, various techniques, including in situ IR.

引用

页码：3766 / 3774

页数：9

共 50 条

[21] Allylmetal-directed addition of 1O2:: Scope, mechanism and synthetic utility
Dussault, PH
Eary, CT
Lee, RJ
Zope, UR
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15): : 2189 - 2204
[22] Asymmetric conjugate 1,6-addition of organocuprates to N-dienoyl oxazolidinones
Sansinenea, Estibaliz
Martinez, Edith Fabiola
Vaca, Jessica
Gonzalez-Alvarez, Carmen M.
Ortiz, Aurelio
TETRAHEDRON, 2024, 166
[23] Organocatalytic Asymmetric 1,6-Addition/1,4-Addition Sequence to 2,4-Dienals for the Synthesis of Chiral Chromans
Poulsen, Pernille H.
Feu, Karla Santos
Paz, Bruno Matos
Jensen, Frank
Jorgensen, Karl Anker
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (28) : 8203 - 8207
[24] Synthesis of isochromene esters utilizing 1,6-addition of nucleophiles to benzopyranylidenetungsten(0) complexes
Kusama, H
Sawada, T
Okita, A
Shiozawa, F
Iwasawa, N
ORGANIC LETTERS, 2006, 8 (06) : 1077 - 1079
[25] MORPHINE SUPPORT STUDIES .2. FORMATION OF THE NEOPINONE CODEINONE RING-SYSTEM VIA INTRAMOLECULAR 1,6-ADDITION OF AN AMINO MOIETY TO A DIENYL KETONE
TOTH, JE
FUCHS, PL
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (13): : 2594 - 2596
[26] Remote stereocontrolled asymmetric 1,6-addition/1,4-addition cascade reactions between cyclic dienones and 2-indolinethiones
Sun, Xiaohua
Fei, Jie
Zou, Chuncheng
Lu, Min
Ye, Jinxing
RSC ADVANCES, 2016, 6 (108): : 106676 - 106679
[27] Polymerization of an azastyrene derivative .1. 1,6-addition polymerization of 2,6-diisopropyl-N-methyleneaniline
Hashidzume, A
Kajiwara, A
Harada, A
Kamachi, M
MACROMOLECULAR RAPID COMMUNICATIONS, 1996, 17 (08) : 529 - 537
[28] CHEMISTRY OF PHENALENIUM SYSTEM .11. 1,6-ADDITION OF PHENALENYLIDENE ONTO CYCLOHEPTATRIENE
MURATA, I
NAKAZAWA, T
IMANISHI, T
TETRAHEDRON LETTERS, 1972, (50) : 5089 - &
[29] 1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes
Gao, Shang
Xu, Xiuyan
Yuan, Zhenbo
Zhou, Haipin
Yao, Hequan
Lin, Aijun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (17) : 3006 - 3012
[30] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers
Chauhan, Pankaj
Kaya, Ugur
Enders, Dieter
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 888 - 912

← 1 2 3 4 5 →