Efficient synthesis of isoxazoles and isoxazolines from aldoximes using Magtrieve™ (CrO2)

被引：61

作者：

Bhosale, Sandeep ^{[1
]}

Kurhade, Santosh ^{[1
]}

Prasad, Uppuleti Viplava ^{[2
]}

Palle, Venkata P. ^{[1
]}

Bhuniya, Debnath ^{[1
]}

机构：

[1] Advinus Therapeut, Drug Discovery Facil, MIDC, Pune 411057, Maharashtra, India

[2] Andhra Univ, Dept Organ Chem, Visakhapatnam 530003, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 27期

关键词：

INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION; NITRILE OXIDES; OXIDATION; 2-ISOXAZOLINES; OXIMES; DERIVATIVES; ANTAGONISTS; GENERATION; LIQUID; POTENT;

D O I：

10.1016/j.tetlet.2009.04.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of aldoximes 1 with Magtrieve (TM) (CrO2) in presence of dipolarophile 3 or 4, furnished a variety of isoxazolines 5a-u and isoxazoles 6a-q as 1,3-dipolar cycloaddition (1,3-DC) products (38 examples; 63-90% isolated yields). In situ formation of a nitrile oxide intermediate was confirmed through isolation of the dimerization product furoxane 2a in absence of any dipolarophile. The methodology has been extended to intramolecular nitrile oxide cycloaddition (INOC) reactions to access highly useful chromane derivatives 7-8 (75-80% isolated yields). Magtrieve (TM), as a new reagent for 1,3-DC reactions, has offered excellent substrate generality and at the same time demonstrated tolerance toward sensitive protecting groups and electron-rich functional groups. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3948 / 3951

页数：4

共 46 条

[1] Peptidomimetics and Peptide Backbone Modifications [J].

Ahn, Jung-Mo ;

Boyle, Nicholas A. ;

MacDonald, Mary T. ;

Janda, Kim D. .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2002, 2 (05) :463-473

[2] Discovery and optimization of substituted piperidines as potent, selective, CNS-penetrant α4β2 nicotinic acetylcholine receptor potentiators [J].

Albrecht, Brian K. ;

Berry, Virginia ;

Boezio, Alessandro A. ;

Cao, Lei ;

Clarkin, Kristie ;

Guo, Wenhong ;

Harmange, Jean-Christophe ;

Hierl, Markus ;

Huang, Liyue ;

Janosky, Brett ;

Knop, Johannes ;

Malmberg, Annika ;

McDermott, Jeff S. ;

Nguyen, Hung Q. ;

Springer, Stephanie K. ;

Waldon, Daniel ;

Woodin, Katrina ;

McDonough, Stefan I. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (19) :5209-5212

[3]

[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD

[4]

BARCO A, 1977, SYNTHESIS-STUTTGART, P837

[5] AN INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION/ELECTROPHILIC CYCLIZATION SEQUENCE TO GIVE CYCLIC ETHERS [J].

BEEBE, X ;

CHIAPPARI, CL ;

KURTH, MJ ;

SCHORE, NE .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7320-7321

[6] An orally bioavailable, functionally selective inverse agonist at the benzodiazepine site of GABAA α5 receptors with cognition enhancing properties [J].

Chambers, MS ;

Atack, JR ;

Carling, RW ;

Collinson, N ;

Cook, SM ;

Dawson, GR ;

Ferris, P ;

Hobbs, SC ;

O'Connor, D ;

Marshall, G ;

Rycroft, W ;

MacLeod, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5829-5832

[7] Synthesis of substituted imidazopyrazines as ligands for the human somatostatin receptor subtype 5 [J].

Contour-Galcéra, MO ;

Poitout, L ;

Moinet, C ;

Morgan, B ;

Gordon, T ;

Roubert, P ;

Thurieau, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (05) :741-745

[8] Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis-Hillman adducts: a new and efficient method for the preparation of nitrile oxides from aldoximes [J].

Das, B ;

Holla, H ;

Mahender, G ;

Banerjee, J ;

Reddy, MR .

TETRAHEDRON LETTERS, 2004, 45 (39) :7347-7350

[9] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

[10]

GRUNANGER P, 1991, CHEM HETEROCYCLIC CO, V49

← 1 2 3 4 5 →