Literature DB >> 19360759

Recent advances in the synthesis of indole and quinoline derivatives through cascade reactions.

José Barluenga1, Félix Rodríguez, Francisco J Fañanás.   

Abstract

Indoles and quinolines are ubiquitous structural motifs in many natural products and biologically active pharmaceuticals. The pursuit of synthetic efficiency has stimulated the design and development of new synthetic strategies to construct these heterocycles. One of the most effective ways of achieving efficiency is to implement reaction cascades, enabling multiple bond-forming and bond-cleaving events to occur in a single synthetic operation, thus circumventing the waste associated with traditional stepwise synthesis. In general, cascade reactions offer the opportunity to access highly functionalized final products from simple starting materials. For all these reasons, it is not a surprise that most of the recently reported methods for the synthesis of indoles and quinolines are based on the use of cascade reactions. In this Focus Review we discuss some of the most representative and interesting recent reports on the synthesis of indoles and quinolines through cascade reactions.

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Year:  2009        PMID: 19360759     DOI: 10.1002/asia.200900018

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  19 in total

1.  Divergent Reactivity of Rhodium(I) Carbenes Derived from Indole Annulations.

Authors:  Xiaoxun Li; Hui Li; Wangze Song; Po-Sen Tseng; Lingyan Liu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-07       Impact factor: 15.336

2.  A multi-component domino reaction for the direct access to polyfunctionalized indoles via intermolecular allylic esterification and indolation.

Authors:  Bo Jiang; Mian-Shuai Yi; Feng Shi; Shu-Jiang Tu; Suresh Pindi; Patrick McDowell; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2011-10-31       Impact factor: 6.222

3.  Platinum-catalyzed tandem indole annulation/arylation for the synthesis of diindolylmethanes and indolo[3,2-b]carbazoles.

Authors:  Dongxu Shu; Gabrielle N Winston-McPherson; Wangze Song; Weiping Tang
Journal:  Org Lett       Date:  2013-08-05       Impact factor: 6.005

4.  Indole synthesis: a review and proposed classification.

Authors:  Douglass F Taber; Pavan K Tirunahari
Journal:  Tetrahedron       Date:  2011-09-23       Impact factor: 2.457

5.  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene.

Authors:  Paul A Allegretti; Khoi Huynh; Tarik J Ozumerzifon; Eric M Ferreira
Journal:  Org Lett       Date:  2015-12-14       Impact factor: 6.005

6.  Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.

Authors:  Hui Li; Xiaoxun Li; Hao-Yuan Wang; Gabrielle N Winston-McPherson; Hao-miao Julie Geng; Ilia A Guzei; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2014-10-21       Impact factor: 6.222

7.  Rhodium(I)-Catalyzed Benzannulation of Heteroaryl Propargylic Esters: Synthesis of Indoles and Related Heterocycles.

Authors:  Xiaoxun Li; Haibo Xie; Xiaoning Fu; Ji-Tian Liu; Hao-Yuan Wang; Bao-Min Xi; Peng Liu; Xiufang Xu; Weiping Tang
Journal:  Chemistry       Date:  2016-06-20       Impact factor: 5.236

8.  Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s.

Authors:  Zhiming Wang; Xingzhu Xu; Zhanshou Gu; Wei Feng; Houjun Qian; Zhengyi Li; Xiaoqiang Sun; Ohyun Kwon
Journal:  Chem Commun (Camb)       Date:  2016-02-14       Impact factor: 6.222

9.  Rhodium- and platinum-catalyzed [4+3] cycloaddition with concomitant indole annulation: synthesis of cyclohepta[b]indoles.

Authors:  Dongxu Shu; Wangze Song; Xiaoxun Li; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-10       Impact factor: 15.336

10.  One-pot phosphine-catalyzed syntheses of quinolines.

Authors:  San Khong; Ohyun Kwon
Journal:  J Org Chem       Date:  2012-09-06       Impact factor: 4.354

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