Literature DB >> 25278635

Regioselectivity of Diels-Alder Reactions Between 6,7-Dehydrobenzofuran and 2-Substituted Furans.

Neil Brown1, Keith R Buszek1.   

Abstract

We describe the first report of the generation of 6,7-dehydrobenzofuran (6,7-benzofuranyne) from 6,7-dihalobenzofurans via metal-halogen exchange and elimination, in a manner similar to our previous work with 6,7-indole arynes. This benzofuranyne undergoes highly regioselective Diels-Alder cycloadditions with 2-substituted furans.

Entities:  

Year:  2012        PMID： 25278635      PMCID： PMC4179875          DOI： 10.1016/j.tetlet.2012.05.118

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  15 in total

1.  New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development.

Authors:  Neil Brown; Diheng Luo; Joseph A Decapo; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-12-23       Impact factor: 2.415

2.  Arynes and cyclohexyne in natural product synthesis.

Authors:  Christian M Gampe; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-15       Impact factor: 15.336

3.  Regioselective Diels-Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes.

Authors:  Neil Brown; Diheng Luo; David Vandervelde; Shaorong Yang; Allen Brassfield; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2009-01-07       Impact factor: 2.415

Review 4.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.

Authors:  Anna J Kochanowska-Karamyan; Mark T Hamann
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

5.  Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries.

Authors:  Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Keith R Buszek
Journal:  ACS Comb Sci       Date:  2011-06-30       Impact factor: 3.784

6.  Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors:  G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2010-11-29       Impact factor: 15.419

7.  Indolynes as electrophilic indole surrogates: fundamental reactivity and synthetic applications.

Authors:  Sarah M Bronner; Kevin B Bahnck; Neil K Garg
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  Indolyne and aryne distortions and nucleophilic regioselectivites.

Authors:  Paul H-Y Cheong; Robert S Paton; Sarah M Bronner; G-Yoon J Im; Neil K Garg; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

9.  Concise synthesis of the bicyclic scaffold of N-methylwelwitindolinone C isothiocyanate via an indolyne cyclization.

Authors:  Xia Tian; Alexander D Huters; Colin J Douglas; Neil K Garg
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  One century of aryne chemistry.

Authors:  Hans Henning Wenk; Michael Winkler; Wolfram Sander
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-03       Impact factor: 15.336
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  4 in total

1.  A Practical, Multi-gram Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-Herbindole C from a Common Intermediate via 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Cross-Coupling Reactions.

Authors:  Nalin Chandrasoma; Sivadarshini Pathmanathan; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

3.  Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling.

Authors:  Nalin Chandrasoma; Neil Brown; Allen Brassfield; Alok Nerurkar; Susana Suarez; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2013-02-20       Impact factor: 2.415

4.  Discovery of EBI-2511: A Highly Potent and Orally Active EZH2 Inhibitor for the Treatment of Non-Hodgkin's Lymphoma.

Authors:  Biao Lu; Xiaodong Shen; Lei Zhang; Dong Liu; Caihua Zhang; Jingsong Cao; Ru Shen; Jiayin Zhang; Dan Wang; Hong Wan; Zhibin Xu; Ming-Hsun Ho; Minsheng Zhang; Lianshan Zhang; Feng He; Weikang Tao
Journal:  ACS Med Chem Lett       Date:  2018-01-29       Impact factor: 4.345
  4 in total

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