Synthesis of isoxazolopyrroloisoquinolines by intramolecular cyclizations of 5-(2-arylethyl)-6-hydroxytetrahydro-4H-pyrrolo[3,4-d]isoxazol-4-ones

被引：15

作者：

Stepakov, Alexander V. ^{[1
]}

Ledovskaya, Maria S. ^{[1
]}

Boitsov, Vitaly M. ^{[2
]}

Molchanov, Alexander P. ^{[1
]}

Kostikov, Rafael R. ^{[1
]}

Gurzhiy, Vladislav V. ^{[1
]}

Starova, Galina L. ^{[1
]}

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] St Petersburg Acad Univ, Nanotechnol Res & Educ Ctr RAS, St Petersburg 195220, Russia

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 40期

基金：

俄罗斯基础研究基金会;

关键词：

Pyrrolo[2,1-a]isoquinolines; Isoxazolopyrroloisoquinolines; Dihydroisoxazoles; Hydroxylactams; N-Acyliminium ion; Intramolecular cyclization; CARBINOLAMINE TUMOR INHIBITORS; ASYMMETRIC-SYNTHESIS; DERIVATIVES; ALKALOIDS; ACID; REDUCTION; CHEMISTRY;

D O I：

10.1016/j.tetlet.2012.07.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5,8a,11a,11b-Tetrahydroisoxazolo[5',4':3,4]pyrrolo[2,1-a]isoquinolin-8(6H)-ones were prepared by intramolecular cyclization of 5-(2-arylethyl)-6-hydroxytetrahydro-4H-pyrrolo[3,4-dlisoxazol-4-ones in the presence of boron trifluoride diethyl etherate. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

引用

页码：5414 / 5417

页数：4

共 48 条

[1] Stereoselective synthesis of the pyrroloisoquinoline ring system [J].

Allin, SM ;

James, SL ;

Martin, WP ;

Smith, TAD .

TETRAHEDRON LETTERS, 2001, 42 (23) :3943-3946

[2] A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-Crispine A [J].

Allin, Steven M. ;

Gaskell, Sean N. ;

Towler, Joannah M. R. ;

Page, Philip C. Bulman ;

Saha, Basu ;

McKenzie, Michael J. ;

Martin, William P. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23) :8972-8975

[3] Enolate amination and derivatization of a pyrroloisoquinoline template towards novel peptidomimetics [J].

Allin, Steven M. ;

Towler, Joannah ;

Gaskell, Sean N. ;

Saha, Basu ;

Martin, William P. ;

Page, Philip C. Bulman ;

Edgar, Mark .

TETRAHEDRON, 2010, 66 (49) :9538-9544

[4] Toward the improvement of the tandem halide displacement/amide coupling spiro-cyclization as a new route to γ-lactam and pyrroloisoquinoline templates [J].

Allous, Iyad ;

Comesse, Sebastien ;

Berkes, Dusan ;

Alkyat, Amar ;

Daich, Adam .

TETRAHEDRON LETTERS, 2009, 50 (31) :4411-4415

[5] Alkaloids from Cynanchum komarovii with inhibitory activity against the tobacco mosaic virus [J].

An, TY ;

Huang, RQ ;

Yang, Z ;

Zhang, DK ;

Li, GR ;

Yao, YC ;

Gao, J .

PHYTOCHEMISTRY, 2001, 58 (08) :1267-1269

[6] VINYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .12. SYNTHESIS AND MURINE ANTINEOPLASTIC ACTIVITY OF BIS[(CARBAMOYLOXY)METHYL] DERIVATIVES OF PYRROLO[2,1-A]ISOQUINOLINE [J].

ANDERSON, WK ;

MCPHERSON, HL ;

NEW, JS ;

RICK, AC .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (10) :1321-1325

[7] VYNYLOGOUS CARBINOLAMINE TUMOR INHIBITORS .23. SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF BIS[[(CARBAMOYL)OXY]METHYL]-SUBSTITUTED PYRROLO[I,1-A]ISOQUINOLINES, PYRROLO[1,2-A]QUINOLINES, PYRROLO[2,1-A]ISOBENZAZEPINES, AND PYRROLO[1,2-A]BENZAZEPINES [J].

ANDERSON, WK ;

HEIDER, AR ;

RAJU, N ;

YUCHT, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (11) :2097-2102

[8] N-Acyliminium Ion Chemistry: Highly Efficient and Versatile Carbon-Carbon Bond Formation by Nucleophilic Substitution of Hydroxy Groups Catalyzed by Sn(NTf2)4 [J].

Ben Othman, Raja ;

Affani, Radouane ;

Tranchant, Marie-Jose ;

Antoniotti, Sylvain ;

Dalla, Vincent ;

Dunach, Elisabet .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (04) :776-780

[9] Asymmetric synthesis of isoquinoline alkaloids [J].

Chrzanowska, M ;

Rozwadowska, MD .

CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370

[10] Pharmacological characterization of (10bS)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline oxalate (YSL-3S) as a new α2-adrenoceptor antagonist [J].

Chung, SH ;

Yook, J ;

Min, BJ ;

Lee, JY ;

Lee, YS ;

Jin, CB .

ARCHIVES OF PHARMACAL RESEARCH, 2000, 23 (04) :353-359

← 1 2 3 4 5 →