Phosphine-mediated cascade reaction of azides with MBH-acetates of acetylenic aldehydes to substituted pyrroles: a facile access to N-fused pyrrolo-heterocycles

被引：38

作者：

Reddy, Chada Raji ^{[1
]}

Reddy, Motatipally Damoder ^{[1
]}

Srikanth, Boinapally ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 21期

关键词：

BAYLIS-HILLMAN REACTION; ACID-CHLORIDES; VINYL AZIDES; ALKALOIDS; SULFONAMIDES; ROSEOPHILIN; DIVERSITY; CHEMISTRY; CATALYST;

D O I：

10.1039/c2ob25272d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot synthesis of substituted pyrroles by a cascade reaction of azides with Morita-Baylis-Hillman acetates of acetylenic aldehydes is described and the reaction is efficiently mediated by triphenyl phosphine at room temperature. Sodium azide is successfully used to provide N-unsubstituted pyrroles, while alkyl azides afforded the corresponding N-alkylated pyrroles through a sequence of allylic substitution/azide reduction/cycloisomerization reactions. The obtained products have provided a new entry to indolizino indoles, pyrrolo isoquinolines and 8-oxo-5,6,7,8-tetrahydroindolizine.

引用

页码：4280 / 4288

页数：9

共 58 条

[1] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope [J].

Aggarwal, VK ;

Emme, I ;

Fulford, SY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :692-700

[2] New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3 [J].

Agnusdei, M ;

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7126-7129

[3] Synthesis of Functionalized Pyrroles via Catalyst- and Solvent-Free Sequential Three-Component Enamine-Azoene Annulation [J].

Attanasi, Orazio A. ;

Favi, Gianfranco ;

Mantellini, Fabio ;

Moscatelli, Giada ;

Santeusanio, Stefania .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2860-2866

[4] One-pot nitro-Mannich/hydroamination cascades for the direct synthesis of 2,5-disubstituted pyrroles using base and gold catalysis [J].

Barber, David M. ;

Sanganee, Hitesh ;

Dixon, Darren J. .

CHEMICAL COMMUNICATIONS, 2011, 47 (15) :4379-4381

[5] A Facile Synthesis of Substituted Indenones and Piperidine-2,6-diones from the Baylis-Hillman Acetates [J].

Basavaiah, Deevi ;

Lenin, Dandamudi V. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (29) :5650-5658

[6] Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].

Basavaiah, Deevi ;

Reddy, Bhavanam Sekhara ;

Badsara, Satpal Singh .

CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674

[7] Organic azides:: An exploding diversity of a unique class of compounds [J].

Bräse, S ;

Gil, C ;

Knepper, K ;

Zimmermann, V .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240

[8] Phosphoramidite accelerated copper(I)-catalyzed [3+2] cycloadditions of azides and alkynes [J].

Campbell-Verduyn, Lachlan S. ;

Mirfeizi, Leila ;

Dierckx, Rudi A. ;

Elsinga, Philip H. ;

Feringa, Ben L. .

CHEMICAL COMMUNICATIONS, 2009, (16) :2139-2141

[9] Formation of a stable 14-helix in short oligomers of furanoid cis-β-sugar-amino acid' [J].

Chandrasekhar, S ;

Reddy, MS ;

Jagadeesh, B ;

Prabhakar, A ;

Rao, MHVR ;

Jagannadh, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13586-13587

[10] Novel bifunctional alkylating agents, 5,10-dihydropyrrolo[1,2-b]isoquinoline derivatives, synthesis and biological activity [J].

Chaniyara, Ravi ;

Kapuriya, Naval ;

Dong, Huajin ;

Lee, Pei-Chih ;

Suman, Sharda ;

Marvania, Bhavin ;

Chou, Ting-Chao ;

Lee, Te-Chang ;

Kakadiya, Rajesh ;

Shah, Anamik ;

Su, Tsann-Long .

BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (01) :275-286

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