Literature DB >> 18665643

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.

Jesse P Waldo1, Saurabh Mehta, Richard C Larock.   

Abstract

A number of new functionally substituted 1-acyl-5-hydroxy-4,5-dihydro-1H-pyrazoles have been prepared in moderate to excellent yields from the corresponding 2-alkyn-1-ones. The resulting dihydropyrazoles undergo dehydration and iodination in the presence of ICl and Li2CO3 at room temperature to provide 1-acyl-4-iodo-1H-pyrazoles.

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Year:  2008        PMID： 18665643      PMCID： PMC3821936          DOI： 10.1021/jo800789p

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


  15 in total

1.  3-Methyl-5-hydroxy-5-trichloromethyl-1H-1-pyrazolcarboxyamide induces antinociception.

Authors:  F R de Souza; M R Fighera; T T Lima; J de Bastiani; I B Barcellos; C E Almeida; M R de Oliveira; H G Bonacorso; A E Flores; C F de Mello
Journal:  Pharmacol Biochem Behav       Date:  2001-03       Impact factor: 3.533

2.  Substituted pyrazoles as hepatoselective HMG-CoA reductase inhibitors: discovery of (3R,5R)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-methyl-benzylcarbamoyl)-2H-pyrazol-3-yl]-3,5-dihydroxyheptanoic acid (PF-3052334) as a candidate for the treatment of hypercholesterolemia.

Authors:  Jeffrey A Pfefferkorn; Chulho Choi; Scott D Larsen; Bruce Auerbach; Richard Hutchings; William Park; Valerie Askew; Lisa Dillon; Jeffrey C Hanselman; Zhiwu Lin; Gina H Lu; Andrew Robertson; Catherine Sekerke; Melissa S Harris; Alexander Pavlovsky; Graeme Bainbridge; Nicole Caspers; Mark Kowala; Bradley D Tait
Journal:  J Med Chem       Date:  2007-12-12       Impact factor: 7.446

3.  4-[3(5)-pyrazolyl]pyridinium salts. A new class of hypoglycemic agents.

Authors:  V J Bauer; H P Dalalian; W J Fanshawe; S R Safir
Journal:  J Med Chem       Date:  1968-09       Impact factor: 7.446

4.  Design, synthesis, and evaluation of 3,4-disubstituted pyrazole analogues as anti-tumor CDK inhibitors.

Authors:  Ronghui Lin; George Chiu; Yang Yu; Peter J Connolly; Shengjian Li; Yanhua Lu; Mary Adams; Angel R Fuentes-Pesquera; Stuart L Emanuel; Lee M Greenberger
Journal:  Bioorg Med Chem Lett       Date:  2007-06-06       Impact factor: 2.823

5.  Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia.

Authors:  Mohamed S Mohammed Ahmed; Atsunori Mori
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

6.  Synthesis and biological evaluation of pyrazolylnaphthoquinones as new potential antiprotozoal and cytotoxic agents.

Authors:  Norma R Sperandeo; Reto Brun
Journal:  Chembiochem       Date:  2003-01-03       Impact factor: 3.164

7.  Synthesis, crystal structure, and activity of pyrazole-based inhibitors of p38 kinase.

Authors:  Matthew J Graneto; Ravi G Kurumbail; Michael L Vazquez; Huey-Sheng Shieh; Jennifer L Pawlitz; Jennifer M Williams; William C Stallings; Lifeng Geng; Ashok S Naraian; Francis J Koszyk; Michael A Stealey; Xiangdong D Xu; Richard M Weier; Gunnar J Hanson; Robert J Mourey; Robert P Compton; Stephen J Mnich; Gary D Anderson; Joseph B Monahan; Rajesh Devraj
Journal:  J Med Chem       Date:  2007-10-19       Impact factor: 7.446

8.  Synthesis and anti-inflammatory activity of fluorinated phenyl styryl ketones and N-phenyl-5-substituted aryl-3-p-(fluorophenyl) pyrazolins and pyrazoles.

Authors:  L V Nargund; V Hariprasad; G R Reedy
Journal:  J Pharm Sci       Date:  1992-09       Impact factor: 3.534

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

Authors:  Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2007-11-03       Impact factor: 4.354

10.  Nonpeptide angiotensin II antagonists derived from 1H-pyrazole-5-carboxylates and 4-aryl-1H-imidazole-5-carboxylates.

Authors:  W T Ashton; S M Hutchins; W J Greenlee; G A Doss; R S Chang; V J Lotti; K A Faust; T B Chen; G J Zingaro; S D Kivlighn
Journal:  J Med Chem       Date:  1993-11-12       Impact factor: 7.446
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