A SIMPLE ROUTE TO FUNCTIONALIZED Δ1-PYRROLINES

被引：20

作者：

Bingham, Matilda ^{[1
]}

Moutrille, Cecile ^{[1
]}

Zard, Samir Z. ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, UMR 7652, Dept Chem, F-91128 Palaiseau, France

来源：

HETEROCYCLES | 2014年 / 88卷 / 02期

关键词：

RADICAL CYCLIZATION; INTRAMOLECULAR ADDITION; OXIMES; O-2,4-DINITROPHENYLOXIMES; DIHYDROPYRROLES;

D O I：

10.3987/COM-13-S(S)94

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of gamma-unsaturated oxime esters with cupric acetate or ferric chloride in acetic acid / t-butanol or in t-butanol alone leads to the formation of vinyl- or chloroalkyl- substituted Delta(1)-pyrrolines in moderate to good yield.

引用

页码：953 / 960

页数：8

共 25 条

[1] A NOVEL AND PRACTICAL ACCESS TO 13-EPI-17-KETOSTEROIDS [J].

BOIVIN, J ;

SCHIANO, AM ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1992, 33 (51) :7849-7852

[2]

Cassayre J, 2000, SYNLETT, P471

[3] Rapid synthesis of substituted pyrrolines and pyrrolidines by nucleophilic ring closure at activated oximes [J].

Chandan, Nandkishor ;

Thompson, Amber L. ;

Moloney, Mark G. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (39) :7863-7868

[4] Phenanthridine Synthesis through Iron-Catalyzed Intramolecular N-Arylation of O-Acetyl Oxime [J].

Deb, Indubhusan ;

Yoshikai, Naohiko .

ORGANIC LETTERS, 2013, 15 (16) :4254-4257

[5]

Fatturoso E., 2008, MODERN ALKALOIDS

[6] Amidinyl radicals: new and useful intermediates for the synthesis of imidazolines and imidazoles [J].

Gennet, D ;

Zard, SZ ;

Zhang, HW .

CHEMICAL COMMUNICATIONS, 2003, (15) :1870-1871

[7] APPLICATIONS OF INTRAMOLECULAR AMIDOMERCURATION .2. SYNTHESIS OF "TRANS-5-HYDROXY-2-PROPYLPIPERIDINE, (+/-)-PSEUDOCONHYDRINE [J].

HARDING, KE ;

BURKS, SR .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (01) :40-44

[8] Photochemical radical cyclization of γ,δ-unsaturated ketone oximes to 3,4-dihydro-2H-pyrroles [J].

Kitamura, M ;

Mori, Y ;

Narasaka, K .

TETRAHEDRON LETTERS, 2005, 46 (14) :2373-2376

[9] Synthesis of quinolines and 2H-dihydropyrroles by nucleophilic substitution at the nitrogen atom of oxime derivatives [J].

Kitamura, M ;

Yoshida, M ;

Kikuchi, T ;

Narasaka, K .

SYNTHESIS-STUTTGART, 2003, (15) :2415-2426

[10] Catalytic radical cyclization of oximes induced by one-electron transfer [J].

Kitamura, Mitsuru ;

Narasaka, Koichi .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (05) :539-547

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