Literature DB >> 16706489

Novel synthesis of highly functionalized pyrazolines and pyrazoles by triphenylphosphine-mediated reaction of dialkyl azodicarboxylate with allenic esters.

Vijay Nair1, A T Biju, Kishor Mohanan, Eringathodi Suresh.   

Abstract

[reaction: see text] Reaction of the Huisgen zwitterion, derived from triphenylphosphine and dialkyl azodicarboxylate, with allenic esters affords highly functionalized pyrazolines and pyrazoles. The crystal structure of pyrazoline derivative 7a showed extensive C-H...O interactions. Pyrazole formation proceeds via a novel nitrogen to carbon migration of the carboalkoxy group.

Entities:  

Year:  2006        PMID： 16706489     DOI： 10.1021/ol0604623

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  KSF: an efficient catalyst for the regioselective synthesis of 1,5-diaryl pyrazoles using Baylis-Hillman adducts.

Authors:  Mohammad Nikpassand; Manouchehr Mamaghani; Khalil Tabatabaeian; Maryam Kupaei Abiazi
Journal:  Mol Divers       Date:  2009-02-21       Impact factor: 2.943

3.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

4.  Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates.

Authors:  Gardner S Creech; Ohyun Kwon
Journal:  Org Lett       Date:  2008-01-04       Impact factor: 6.005

5.  Stereoselective synthesis of cis- or trans-3,5-disubstituted pyrazolidines via Pd-catalyzed carboamination reactions: use of allylic strain to control product stereochemistry through N-substituent manipulation.

Authors:  Natalie C Giampietro; John P Wolfe
Journal:  J Am Chem Soc       Date:  2008-09-06       Impact factor: 15.419

6.  Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.

Authors:  Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Journal:  Beilstein J Org Chem       Date:  2012-10-09       Impact factor: 2.883
  6 in total

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