Literature DB >> 17979295

The synthesis of highly substituted isoxazoles by electrophilic cyclization: an efficient synthesis of valdecoxib.

Jesse P Waldo1, Richard C Larock.   

Abstract

A large number of functionally substituted 2-alkyn-1-one O-methyl oximes have been cyclized under mild reaction conditions in the presence of ICl to give the corresponding 4-iodoisoxazoles in moderate to excellent yields. The resulting 4-iodoisoxazoles undergo various palladium-catalyzed reactions to yield 3,4,5-trisubstituted isoxazoles, including valdecoxib.

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Year:  2007        PMID： 17979295      PMCID： PMC2529460          DOI： 10.1021/jo701942e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  35 in total

1.  Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization.

Authors:  Dawei Yue; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

2.  Novel class of potent 4-arylalkyl substituted 3-isoxazolol GABA(A) antagonists: synthesis, pharmacology, and molecular modeling.

Authors:  Bente Frølund; Anne T Jørgensen; Lena Tagmose; Tine B Stensbøl; Henrik T Vestergaard; Christine Engblom; Uffe Kristiansen; Connie Sanchez; Povl Krogsgaard-Larsen; Tommy Liljefors
Journal:  J Med Chem       Date:  2002-06-06       Impact factor: 7.446

3.  Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes.

Authors:  Qinhua Huang; Jack A Hunter; Richard C Larock
Journal:  J Org Chem       Date:  2002-05-17       Impact factor: 4.354

4.  A novel palladium-mediated coupling approach to 2,3-disubstituted benzo(b)thiophenes and its application to the synthesis of tubulin binding agents.

Authors:  B L Flynn; P Verdier-Pinard; E Hamel
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

5.  Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization.

Authors:  Dawei Yue; Tuanli Yao; Richard C Larock
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

6.  Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.

Authors:  Dawei Yue; Richard C Larock
Journal:  J Org Chem       Date:  2002-03-22       Impact factor: 4.354

7.  Optimization of a tertiary alcohol series of phosphodiesterase-4 (PDE4) inhibitors: structure-activity relationship related to PDE4 inhibition and human ether-a-go-go related gene potassium channel binding affinity.

Authors:  Richard W Friesen; Yves Ducharme; Richard G Ball; Marc Blouin; Louise Boulet; Bernard Côté; Richard Frenette; Mario Girard; Daniel Guay; Zheng Huang; Thomas R Jones; France Laliberté; Joseph J Lynch; Joseph Mancini; Evelyn Martins; Paul Masson; Eric Muise; Douglas J Pon; Peter K S Siegl; Angela Styhler; Nancy N Tsou; Mervyn J Turner; Robert N Young; Yves Girard
Journal:  J Med Chem       Date:  2003-06-05       Impact factor: 7.446

8.  Synthesis of 3-iodoindoles by electrophilic cyclization of N,N-dialkyl-2-(1-alkynyl)anilines.

Authors:  Dawei Yue; Richard C Larock
Journal:  Org Lett       Date:  2004-03-18       Impact factor: 6.005

9.  Efficient syntheses of heterocycles and carbocycles by electrophilic cyclization of acetylenic aldehydes and ketones.

Authors:  Dawei Yue; Nicola Della Cà; Richard C Larock
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

10.  Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles: a versatile trigger for assembling oxygen heterocycles.

Authors:  José Barluenga; Henar Vázquez-Villa; Alfredo Ballesteros; José M González
Journal:  J Am Chem Soc       Date:  2003-07-30       Impact factor: 15.419
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  19 in total

Review 1.  Recent methodologies toward the synthesis of valdecoxib: a potential 3,4-diarylisoxazolyl COX-II inhibitor.

Authors:  Sureshbabu Dadiboyena; Adel Nefzi
Journal:  Eur J Med Chem       Date:  2010-08-06       Impact factor: 6.514

Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

3.  Synthesis and SAR of novel isoxazoles as potent c-jun N-terminal kinase (JNK) inhibitors.

Authors:  Yuanjun He; Derek Duckett; Weimin Chen; Yuan Yuan Ling; Michael D Cameron; Li Lin; Claudia H Ruiz; Philip V Lograsso; Theodore M Kamenecka; Marcel Koenig
Journal:  Bioorg Med Chem Lett       Date:  2013-12-04       Impact factor: 2.823

4.  One Pot Spiropyrazoline Synthesis via Intramolecular Cyclization/Methylation.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2011-05-18       Impact factor: 2.415

5.  Synthesis of 3-sulfenyl- and 3-selenylindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal alkynes, followed by n-Bu(4)NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Feng Shi; Richard C Larock
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  Room temperature ICl-induced dehydration/iodination of 1-acyl-5-hydroxy-4,5-dihydro-1H-pyrazoles. a selective route to substituted 1-acyl-4-iodo-1H-pyrazoles.

Authors:  Jesse P Waldo; Saurabh Mehta; Richard C Larock
Journal:  J Org Chem       Date:  2008-07-30       Impact factor: 4.354

7.  Solution phase synthesis of a diverse library of highly substituted isoxazoles.

Authors:  Jesse P Waldo; Saurabh Mehta; Benjamin Neuenswander; Gerald H Lushington; Richard C Larock
Journal:  J Comb Chem       Date:  2008-08-01

8.  A novel synthetic route to 3-sulfenyl- and 3-selenylindoles by n-Bu4NI-induced electrophilic cyclization.

Authors:  Yu Chen; Chul-Hee Cho; Richard C Larock
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

9.  Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.

Authors:  James S Oakdale; Rakesh K Sit; Valery V Fokin
Journal:  Chemistry       Date:  2014-07-24       Impact factor: 5.236

10.  Competition studies in alkyne electrophilic cyclization reactions.

Authors:  Saurabh Mehta; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354
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