A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds

被引：26

作者：

Tripoteau, Fabien ^{[1
]}

Eberlin, Ludovic ^{[1
]}

Fox, Mark A. ^{[2
]}

Carboni, Bertrand ^{[1
]}

Whiting, Andrew ^{[2
]}

机构：

[1] Univ Rennes 1, CNRS, UMR 6626, Inst Sci Chim Rennes, F-35042 Rennes, France

[2] Univ Durham, Deptartment Chem, Ctr Sustainable Chem Proc, Durham DH1 3LE, England

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 47期

关键词：

DIELS-ALDER REACTIONS; PYRROLIDINE DERIVATIVES; NITROSO; CONSTRUCTION; ACCESS; CYCLOADDITIONS; HETEROCYCLES; CHEMISTRY; ANALOGS; ROUTE;

D O I：

10.1039/c3cc42227e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot hetero-Diels-Alder/ring contraction cascade is presented from the reaction of 1-boronodienes and arylnitroso derivatives to derive N-arylpyrroles in moderate to good yields (up to 82%).

引用

页码：5414 / 5416

页数：3

共 45 条

[1] β-Alkoxy-γ-amino Aldehydes by Internal Redox Ring Cleavages of Carbohydrate-Derived Enantiopure 1,2-Oxazines and Preparation of Heterocycles with Aminopolyol Side Chain [J].

Al-Harrasi, Ahmed ;

Bouche, Lea ;

Zimmer, Reinhold ;

Reissig, Hans-Ulrich .

SYNTHESIS-STUTTGART, 2011, (01) :109-118

[2] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2006, 62 (31) :7213-7256

[3] Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye grass and tall fescue [J].

Blakemore, PR ;

Kim, SK ;

Schulze, VK ;

White, JD ;

Yokochi, AFT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (15) :1831-1845

[4] The Nitrosocarbonyl Hetero-Diels-Alder Reaction as a Useful Tool for Organic Syntheses [J].

Bodnar, Brian S. ;

Miller, Marvin J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (25) :5629-5646

[5] Synthesis of novel carbohydrate mimetics via 1,2-oxazines [J].

Bouche, Lea ;

Reissig, Hans-Ulrich .

PURE AND APPLIED CHEMISTRY, 2012, 84 (01) :23-36

[6] A New Approach to Neuraminic Acid Analogues via 1,2-Oxazines [J].

Bressel, Bettina ;

Reissig, Hans-Ulrich .

ORGANIC LETTERS, 2009, 11 (03) :527-530

[7] Synthesis of polysubstituted pyrroles from nitroso-Diels-Alder cyloadducts [J].

Calvet, G ;

Blanchard, N ;

Kouklovsky, C .

SYNTHESIS-STUTTGART, 2005, (19) :3346-3354

[8] 1,3-dipolar cycloadditions to unsaturated organoboranes .3. Regio- and stereocontrolled access to boronic ester substituted isoxazolidines. [J].

Carboni, B ;

Ollivault, M ;

LeBouguenec, F ;

Carrie, R ;

Jazouli, M .

TETRAHEDRON LETTERS, 1997, 38 (38) :6665-6668

[9] Copper(II)-Catalyzed Room Temperature Aerobic Oxidation of Hydroxamic Acids and Hydrazides to Acyl-Nitroso and Azo Intermediates, and Their Diels-Alder Trapping [J].

Chaiyaveij, Duangduan ;

Cleary, Leah ;

Batsanov, Andrei S. ;

Marder, Todd B. ;

Shea, Kenneth J. ;

Whiting, Andrew .

ORGANIC LETTERS, 2011, 13 (13) :3442-3445

[10] A SIMPLE ONE-POT SYNTHESIS OF THE TRICYCLIC MITOMYCIN SKELETON [J].

DEFOIN, A ;

FRITZ, H ;

GEFFROY, G ;

STREITH, J .

TETRAHEDRON LETTERS, 1986, 27 (27) :3135-3138

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