Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide

被引：1

作者：

Jebali, Khaoula ^{[1
]}

Arfaoui, Aicha ^{[1
]}

Saadi, Fatma ^{[1
]}

Lebreton, Jacques ^{[2
]}

Amri, Hassen ^{[1
]}

机构：

[1] El Manar Univ, Lab Select Organ Synth & Biol Act, Fac Sci, Tunis 2092, Tunisia

[2] Fac Sci & Tech, CNRS UMR, Synth Organ Lab, Nantes, France

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 23期

关键词：

5-Exo-trig cyclization; primary amines; Z-ethyl; 3-bromomethyl-4-oxopent-2-enoate; pyrrol-2(5H)-ones; METHYLENE-GAMMA-LACTAMS; WITTIG-HORNER REACTION; BIOLOGICAL EVALUATION; HIV PROTEASE; ANALOGS; INHIBITORS; DESIGN; DERIVATIVES; ALKALOIDS; FUMARATE;

D O I：

10.1080/00397911.2014.938273

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a simple and efficient protocol for accessing some unsaturated heterocyclic compounds in a direct evaluation of allyl bromide as Z-ethyl 3-bromomethyl-4-oxopent-2-enoate. The latter reacts with primary amines via two successive nucleophilic substitutions followed by a 5-exo-trig cyclization to produce selectively 4-acetyl-1-alkyl-1H-pyrrol-2(5H)-ones in good yields.

引用

页码：3400 / 3407

页数：8

共 40 条

[11] Heck arylations of N-acyl-3-pyrroline and N-acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts.: Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues [J].

Carpes, MJS ;

Correia, CRD .

TETRAHEDRON LETTERS, 2002, 43 (05) :741-744

[12] Synthesis of reactive gamma-lactams related to penicillins and cephalosporins [J].

Davies, GM ;

Hitchcock, PB ;

Loakes, D ;

Young, DW .

TETRAHEDRON LETTERS, 1996, 37 (31) :5601-5604

[13]

DEKKERS AWJ, 1971, TETRAHEDRON LETT, P489

[14] An efficient synthesis of β,γ,γ-trisubstituted-α-diethoxyphosphoryl-γ-lactams: a convenient approach to α-methylene-γ-lactams [J].

Deredas, Dariusz ;

Albrecht, Lukasz ;

Krawczyk, Henryk .

TETRAHEDRON LETTERS, 2013, 54 (24) :3088-3090

[15] A short dipolar cycloaddition approach to gamma-lactam alkaloids from Cynometra hankei [J].

Fishwick, CWG ;

Foster, RJ ;

Carr, RE .

TETRAHEDRON LETTERS, 1996, 37 (22) :3915-3918

[16] Chiral 3-hydroxypyrrolidin-2-ones.: Part 2:: Stereodivergent synthesis of conformationally restricted analogues of β-homoserine [J].

Galeazzi, R ;

Martelli, G ;

Natali, D ;

Orena, M ;

Rinaldi, S .

TETRAHEDRON-ASYMMETRY, 2005, 16 (10) :1779-1787

[17] RECENT DEVELOPMENTS IN 2-PYRROLIDINONE-CONTAINING NOOTROPICS [J].

GAMZU, ER ;

HOOVER, TM ;

GRACON, SI ;

NINTEMAN, MV .

DRUG DEVELOPMENT RESEARCH, 1989, 18 (03) :177-189

[18] STEREOSPECIFIC FORMATION OF A VINYL SULFIDE VIA A SULFONIUM YLIDE-SALT COUPLING REACTION [J].

GARBERS, CF ;

LABUSCHA.AJ ;

MEYER, CJ ;

SCHNEIDE.DF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (18) :2016-2019

[19] Three-component condensation of methyl acylpyruvates with aromatic aldehydes and ethylenediamine. Chemical properties of the products [J].

Gein, VL ;

Kasimova, NN .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2005, 75 (02) :254-260

[20] SYNTHESIS AND ANTIINFLAMMATORY ACTIVITIES OF 3-(3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENE)PYRROLIDIN-2-ONES [J].

IKUTA, H ;

SHIROTA, H ;

KOBAYASHI, S ;

YAMAGISHI, Y ;

YAMADA, K ;

YAMATSU, I ;

KATAYAMA, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :1995-1998

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