Facile, diastereoselective synthesis of functionally enriched hexahydroisoquinolines, hexahydroisoquinolones and hexahydroisochromones via inter-/intramolecular amidolysis of C-3 functionalized 2-azetidinones

被引：17

作者：

Mehra, Vishu ^{[1
]}

Kumar, Vipan ^{[1
]}

机构：

[1] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

来源：

TETRAHEDRON | 2013年 / 69卷 / 19期

关键词：

beta-Lactam synthon approach; Hexahydroisoquinolines; Hexahydroisoquinolones/hexahydroisochromones; Tandem intermolecular amidolysis-cyclization; Inter-/intramolecular amidolysis; ONE-POT SYNTHESIS; ALLENYL-BETA-LACTAMS; BUILDING-BLOCKS; ISOQUINOLINE ALKALOIDS; ASYMMETRIC-SYNTHESIS; RING EXPANSION; SYNTHON; DERIVATIVES; HETEROCYCLES; ALKYNES;

D O I：

10.1016/j.tet.2013.03.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe herein the synthetic utility of beta-lactam synthon protocol for the convenient and diastereoselective synthesis of functionally decorated hexahydroisoquinolines, hexahydroisoquinolones and hexahydroisochromones. Since the described protocol does not include the use of highly functionalized intermediates, stringent conditions or toxic reagents, the developed methodology does not suffer from the typical intricacies associated with the conventional protocols. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3857 / 3866

页数：10

共 4 条

[1] Facile diastereoselective synthesis of functionally enriched hydantoins via base-promoted intramolecular amidolysis of C-3 functionalized azetidin-2-ones
Mehra, Vishu
Kumar, Vipan
TETRAHEDRON LETTERS, 2013, 54 (45) : 6041 - 6044
[2] Diastereoselective synthesis of 2,3-disubstituted 1-arylazetidines via NaBH4-promoted facile reduction of C-3 functionalized azetidin-2-ones
Mehra, Vishu
Neetu
Kumar, Vipan
TETRAHEDRON LETTERS, 2013, 54 (35) : 4763 - 4766
[3] Orthogonal and auto-tandem catalysis:: Synthesis of dipyrido[1,2-a:2′,3′-d]imidazole and its benzo and aza analogues via inter- and intramolecular C-N bond formation
Loones, KTJ
Maes, BUW
Meyers, C
Deruytter, J
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 260 - 264
[4] Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles
Kumar, S. Vijay
Saraiah, B.
Parameshwarappa, G.
Ila, H.
Verma, Girijesh K.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 7961 - 7978

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