Literature DB >> 22983883

Tandem synthesis of highly functionalized pyrazole derivatives from terminal alkynes, sulfonyl azides, diethyl azadicarboxylate, and sodium arylsulfinates.

Issa Yavari1, Manijeh Nematpour.   

Abstract

The reaction between ketenimine intermediates [generated from terminal alkynes and sulfonyl azides], diethyl azadicarboxylate, and sodium arylsulfinates in N, N-dimethylformamide at room temperature, affords ethyl 2,3-dihydro-3-oxo-4-phenyl-2-tosyl-5-(tosylamino)pyrazole-1-carboxylates in moderate-to-good yields. When diisopropyl azadicarboxylate was used as the ester component, diisopropyl 1-arylsulfonyl-2-{[aryl(alkyl)sulfonyl]-2-phenylethanimidoyl}-1,2-hydrazinedicarboxylates were obtained.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22983883     DOI： 10.1007/s11030-012-9393-y

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  11 in total

1.  Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib).

Authors:  T D Penning; J J Talley; S R Bertenshaw; J S Carter; P W Collins; S Docter; M J Graneto; L F Lee; J W Malecha; J M Miyashiro; R S Rogers; D J Rogier; S S Yu; E G Burton; J N Cogburn; S A Gregory; C M Koboldt; W E Perkins; K Seibert; A W Veenhuizen; Y Y Zhang; P C Isakson
Journal:  J Med Chem       Date:  1997-04-25       Impact factor: 7.446

2.  Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity.

Authors:  Eun Jeong Yoo; Mårten Ahlquist; Seok Hwan Kim; Imhyuck Bae; Valery V Fokin; K Barry Sharpless; Sukbok Chang
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 3.  Cu-catalyzed azide-alkyne cycloaddition.

Authors:  Morten Meldal; Christian Wenzel Tornøe
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

Review 4.  From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles.

Authors:  Santos Fustero; María Sánchez-Roselló; Pablo Barrio; Antonio Simón-Fuentes
Journal:  Chem Rev       Date:  2011-08-01       Impact factor: 60.622

5.  Domino Michael-O-alkylation: one-pot synthesis of dialkyl 4-oxo-2,3-dihydro-2,3-furandicarboxylates.

Authors:  Issa Yavari; Mehdi Sirouspour; Sanaz Souri
Journal:  Mol Divers       Date:  2010-09-10       Impact factor: 2.943

Review 6.  Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides.

Authors:  Jason E Hein; Valery V Fokin
Journal:  Chem Soc Rev       Date:  2010-03-04       Impact factor: 54.564

7.  5-Heteroatom substituted pyrazoles as canine COX-2 inhibitors. Part III: molecular modeling studies on binding contribution of 1-(5-methylsulfonyl)pyrid-2-yl and 4-nitrile.

Authors:  Subas M Sakya; Xinjun Hou; Martha L Minich; Bryson Rast; Andrei Shavnya; Kristin M L DeMello; Hengmiao Cheng; Jin Li; Burton H Jaynes; Donald W Mann; Carol F Petras; Scott B Seibel; Michelle L Haven
Journal:  Bioorg Med Chem Lett       Date:  2006-11-15       Impact factor: 2.823

8.  Regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles from N-arylhydrazones and nitroolefins.

Authors:  Xiaohu Deng; Neelakandha S Mani
Journal:  J Org Chem       Date:  2008-02-16       Impact factor: 4.354

9.  Parallel synthesis of potent, pyrazole-based inhibitors of Helicobacter pylori dihydroorotate dehydrogenase.

Authors:  Tasir S Haque; Seifu Tadesse; Jovita Marcinkeviciene; M John Rogers; Christine Sizemore; Lisa M Kopcho; Karen Amsler; Lisa D Ecret; Dong Liang Zhan; Frank Hobbs; Andrew Slee; George L Trainor; Andrew M Stern; Robert A Copeland; Andrew P Combs
Journal:  J Med Chem       Date:  2002-10-10       Impact factor: 7.446

10.  Reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of bidentate nucleophiles.

Authors:  Issa Yavari; Maryam Sabbaghan; Zinatossadat Hossaini
Journal:  Mol Divers       Date:  2006-11-23       Impact factor: 3.364
View more
  4 in total

1.  Sulfonoketenimides as key intermediates for the synthesis of 2-thioxo-2H-1,3-thiazines and 2-arylimino-2H-1,3-thiazines.

Authors:  Issa Yavari; Manijeh Nematpour; Tahereh Damghani
Journal:  Mol Divers       Date:  2013-09-20       Impact factor: 2.943

2.  A tandem synthesis of 5-sulfonylimino-2-imidazolones from sulfonoketenimides and dialkyl azodicarboxylates.

Authors:  Issa Yavari; Manijeh Nematpour; Ehsan Ghanbari
Journal:  Mol Divers       Date:  2014-06-13       Impact factor: 2.943

3.  A tandem synthesis of functionalized azet-2(1H)-ones and azet-2(1H)-thiones.

Authors:  Issa Yavari; Manijeh Nematpour; Mohammad J Bayat
Journal:  Mol Divers       Date:  2013-09-17       Impact factor: 2.943

4.  A facile and regioselective one-pot synthesis of novel pyrazolo[1[Formula: see text],5[Formula: see text]:1,2]pyrrolo[3,4-b]quinoline-2,3-dicarboxylate hybrids via intramolecular Wittig reaction.

Authors:  Tahere Hosseyni Largani; Gholamhasan Imanzadeh; Nader Noroozi Pesyan; Ertan Şahin; Amir Nasser Shamkhali; Behrouz Notash
Journal:  Mol Divers       Date:  2017-10-23       Impact factor: 2.943
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.