Literature DB >> 20161257

1,3-Dipolar cycloaddition of arynes with azomethine imines: synthesis of 1,2-dihydropyrazolo[1,2-a]indazol-3(9H)-ones.

Feng Shi1, Raffaella Mancuso, Richard C Larock.   

Abstract

A [3+2] 1,3-dipolar cycloaddition reaction of arynes with stable azomethine imines has been developed. The reaction rapidly assembles tricyclic pyrazoloindazolone derivatives in moderate yields under mild reaction conditions.

Entities:  

Year:  2009        PMID: 20161257      PMCID: PMC2699673          DOI: 10.1016/j.tetlet.2009.04.102

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


  9 in total

1.  Intramolecular [4 + 2] cycloadditions of benzynes with conjugated enynes, arenynes, and dienes.

Authors:  Martin E Hayes; Hiroshi Shinokubo; Rick L Danheiser
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  Utilization of Tetrabutylammonium Triphenyldifluorosilicate as a Fluoride Source for Silicon-Carbon Bond Cleavage.

Authors:  Anthony S. Pilcher; Philip DeShong
Journal:  J Org Chem       Date:  1996-10-04       Impact factor: 4.354

3.  Orthogonal synthesis of indolines and isoquinolines via aryne annulation.

Authors:  Christopher D Gilmore; Kevin M Allan; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2008-01-15       Impact factor: 15.419

4.  Kinetic resolutions of azomethine imines via copper-catalyzed [3 + 2] cycloadditions.

Authors:  Andrés Suárez; C Wade Downey; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

5.  An efficient, facile, and general synthesis of 1h-indazoles by 1,3-dipolar cycloaddition of arynes with diazomethane derivatives.

Authors:  Tienan Jin; Yoshinori Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Regioselective synthesis of 3-(2-hydroxyaryl)pyridines via arynes and pyridine N-oxides.

Authors:  Cristiano Raminelli; Zhijian Liu; Richard C Larock
Journal:  J Org Chem       Date:  2006-06-09       Impact factor: 4.354

7.  Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides.

Authors:  Feng Shi; Jesse P Waldo; Yu Chen; Richard C Larock
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005

8.  Synthesis of indazoles by the [3+2] cycloaddition of diazo compounds with arynes and subsequent acyl migration.

Authors:  Zhijian Liu; Feng Shi; Pablo D G Martinez; Cristiano Raminelli; Richard C Larock
Journal:  J Org Chem       Date:  2007-12-08       Impact factor: 4.354

9.  A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.

Authors:  Ryo Shintani; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

  9 in total
  7 in total

1.  Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Authors:  Chunrui Wu; Yuesi Fang; Richard C Larock; Feng Shi
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

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.  Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-02-16       Impact factor: 4.354

4.  Facile access to regio- and stereoselective synthesis of highly functionalized spiro[indoline-3,2'-pyrrolidines] incorporating a pyrene moiety: experimental, photophysical and theoretical approach.

Authors:  Essam M Hussein; Ziad Moussa; Nizar El Guesmi; Saleh A Ahmed
Journal:  RSC Adv       Date:  2018-07-03       Impact factor: 4.036

5.  5,6-Dimeth-oxy-4',5'-diphenyl-indane-2-spiro-3'-pyrrolidine-2'-spiro-3''-indoline-1,2''-dione.

Authors:  Mohamed Ashraf Ali; Rusli Ismail; Soo Choon Tan; Chin Sing Yeap; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-11

6.  5-[(E)-2-Bromo-benzyl-idene]-8-(2-bromo-phen-yl)-2-hy-droxy-10-methyl-3,10-di-aza-hexa-cyclo-[10.7.1.1.0.0.0]henicosa-1(20),12,14,16,18-pentaen-6-one.

Authors:  Raju Suresh Kumar; Hasnah Osman; Mohamed Ashraf Ali; Mohd Mustaqim Rosli; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-08-21

7.  Regio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.

Authors:  Perumal Prabhakaran; Perumal Rajakumar
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

  7 in total

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