Construction of novel spiroisoxazolines via intramolecular cyclization/methylation

被引：11

作者：

Ellis, Erick D. ^{[1
]}

Xu, Jianping ^{[1
]}

Valente, Edward J. ^{[2
]}

Hamme, Ashton T., II ^{[1
]}

机构：

[1] Jackson State Univ, Dept Chem & Biochem, Coll Sci Engn & Technol, Jackson, MS 39217 USA

[2] Univ Portland, Dept Chem, Portland, OR 97203 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 39期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

Intramolecular cyclization; Cycloaddition; Regioselectivity; Spirocycles; Heterocycles; 1,3-DIPOLAR CYCLOADDITION REACTION; MARINE SPONGE METABOLITES; OXIDATIVE CYCLIZATION; AEROTHIONIN; ALKALOIDS; ISOXAZOLINES; VERONGAMINE; REACTIVITY; ACCESS;

D O I：

10.1016/j.tetlet.2009.07.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Improved yields for the syntheses of a variety of spiroisoxazolines were achieved through intramolecular cyclization/methylation reactions of functionalized 5,5-disubstituted isoxazolines in one reaction vessel. Aromatic ring containing nitrile oxides and disubstituted geminal alkenes reacted in a 1,3-dipolar fashion to afford the corresponding 5,5-isoxazoline. A comparison of the relative location of the nucleophile and electrophile on the isoxazoline and two different ester functional groups was performed in order to determine the best isoxazoline system for the intramolecular cyclization/methylation reaction. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5516 / 5519

页数：4

共 50 条

[1] Spiroisoxazoline synthesis via intramolecular cyclization/methylation
Xu, Jianping
Wang, Jun
Ellis, Erick D.
Hamme, Ashton T., II
SYNTHESIS-STUTTGART, 2006, 22 (22): : 3815 - 3818
[2] One pot spiropyrazoline synthesis via intramolecular cyclization/methylation
Dadiboyena, Sureshbabu
Hamme, Ashton T., II
TETRAHEDRON LETTERS, 2011, 52 (20) : 2536 - 2539
[3] ORGN 347-Spiropyrazoline synthesis via intramolecular cyclization/methylation
Dadiboyena, Sureshbabu
Hamme, Ashton T., II
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
[4] A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride
Hirotani, S
Kaji, E
TETRAHEDRON, 1999, 55 (14) : 4255 - 4270
[5] Construction of Structurally Inspiring Spiroisoxazolines
Dadiboyena, Sureshbabu
CURRENT ORGANIC SYNTHESIS, 2013, 10 (05) : 661 - 682
[6] A synthetic use of the intramolecular alkyl migration process in indolylborates for intramolecular cyclization: a novel construction of carbazole derivatives
Ishikura, M
Kato, H
TETRAHEDRON, 2002, 58 (49) : 9827 - 9838
[7] AN INTRAMOLECULAR COBALT CYCLIZATION FOR THE CONSTRUCTION OF SUBSTITUTED PYRROLIDINES
BALDWIN, JE
MOLONEY, MG
PARSONS, AF
TETRAHEDRON, 1992, 48 (42) : 9373 - 9384
[8] A Novel Synthesis of Isoflavones via Copper(I)-Catalyzed Intramolecular Cyclization Reaction
Li, Qiu-Lian
Liu, Qi-Lun
Ge, Zhi-Yuan
Zhu, Yong-Ming
HELVETICA CHIMICA ACTA, 2011, 94 (07) : 1304 - 1309
[9] The synthesis of a novel benzodiazocine via an intramolecular Staudinger/Aza-Wittig cyclization
ONeil, IA
Murray, CL
Potter, AJ
Kalindjian, SB
TETRAHEDRON LETTERS, 1997, 38 (20) : 3609 - 3610
[10] The synthesis of a novel benzodiazocine via an intramolecular Staudinger/aza-Wittig cyclization
O'Neil, I. A.
Murray, C. L.
Potter, A. J.
Kalindjian, S. B.
Tetrahedron Letters, 38 (20):

← 1 2 3 4 5 →