Literature DB >> 23506186

Highly selective domino multicyclizations for forming polycyclic fused acridines and azaheterocyclic skeletons.

Bo Jiang1, Xue Wang, Hai-Wei Xu, Man-Su Tu, Shu-Jiang Tu, Guigen Li.   

Abstract

Highly selective four-component domino multicyclizations for the synthesis of new fused acridines and azaheterocyclic skeletons have been established by mixing common reactants in isobutyric acid under microwave irradiation. The reactions proceeded at fast rates and were conducted to completion within 20-30 min. Up to seven new chemical bonds, four rings, and four stereocenters were assembled in a convenient one-pot operation. The resulting hexacyclic and pentacyclic fused acridines and their stereochemistry have been fully characterized and determined by X-ray structural analysis.

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Year:  2013        PMID: 23506186      PMCID: PMC3635953          DOI: 10.1021/ol400322v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  30 in total

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4.  Four-component domino reaction leading to multifunctionalized quinazolines.

Authors:  Bo Jiang; Shu-Jiang Tu; Parminder Kaur; Walter Wever; Guigen Li
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

5.  An efficient synthesis of pyrrolo[2,3,4-kl]acridin-1-one derivatives catalyzed by L-proline.

Authors:  Huiyuan Wang; Lili Li; Wei Lin; Pan Xu; Zhibin Huang; Daqing Shi
Journal:  Org Lett       Date:  2012-08-24       Impact factor: 6.005

6.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
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7.  Gold-catalyzed three-component coupling: oxidative oxyarylation of alkenes.

Authors:  Asa D Melhado; William E Brenzovich; Aaron D Lackner; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

8.  Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.

Authors:  Dawei Ma; Qian Cai
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

9.  The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.

Authors:  Lutz F Tietze; Tom Kinzel; C Christian Brazel
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

10.  Conjugate addition-dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: application to the total synthesis of (+/-)-yohimbenone.

Authors:  Chad J Stearman; Michael Wilson; Albert Padwa
Journal:  J Org Chem       Date:  2009-05-01       Impact factor: 4.354

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  7 in total

1.  Cascade bicyclizations of o-alkynyl aldehydes with thiazolium salts: a new access toward poly-functionalized indeno[2,1-b]pyrroles.

Authors:  Peng Zhou; Wen-Juan Hao; Jin-Peng Zhang; Bo Jiang; Guigen Li; Shu-Jiang Tu
Journal:  Chem Commun (Camb)       Date:  2015-08-21       Impact factor: 6.222

2.  Synthesis of enaminones and their difluoroboron complexes through domino aryl migration.

Authors:  Zheng Yang; Bo Jiang; Wen-Juan Hao; Peng Zhou; Shu-Jiang Tu; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

3.  Four-component strategy for selective synthesis of azepino[5,4,3-cd]indoles and pyrazolo[3,4-b]pyridines.

Authors:  Bo Jiang; Qin Ye; Wei Fan; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  Chem Commun (Camb)       Date:  2014-06-11       Impact factor: 6.222

4.  New Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines.

Authors:  Wen-Juan Hao; Peng Zhou; Fei-Yue Wu; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  European J Org Chem       Date:  2016-03-29

5.  Divergent synthesis of dual 1,4-dihydropyridines with different substituted patterns from enaminones and aldehydes through domino reactions.

Authors:  Fu-Jun Liu; Tian-Tian Sun; Yun-Gang Yang; Chao Huang; Xue-Bing Chen
Journal:  RSC Adv       Date:  2018-04-03       Impact factor: 3.361

6.  Four-component bicyclization approaches to skeletally diverse pyrazolo[3,4-b]pyridine derivatives.

Authors:  Xing-Jun Tu; Wen-Juan Hao; Qin Ye; Shuang-Shuang Wang; Bo Jiang; Guigen Li; Shu-Jiang Tu
Journal:  J Org Chem       Date:  2014-11-04       Impact factor: 4.354

7.  Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives.

Authors:  Xue-Bing Chen; Sheng-Li Xiong; Zhi-Xu Xie; Yong-Chao Wang; Wei Liu
Journal:  ACS Omega       Date:  2019-07-09
  7 in total

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