Literature DB >> 24882890

Synthesis and Tautomerism of Spiro-Pyrazolines.

Sureshbabu Dadiboyena1, Edward J Valente2, Ashton T Hamme1.   

Abstract

An experimental study on the synthesis, tautomerism and acid promoted structural changes of spiro-pyrazolines is described. The target was achieved through a [3+2]-dipolar cycloaddition of an alkene with nitrile imines generated in situ and was isolated in high yield. The synthesized cycloadduct displayed a tendency to exhibit an imine-enamine type of tautomerism as evidenced by X-ray crystal and NMR studies. Furthermore, addition of an acid resulted in the transformation of an imine tautomer to an enamine. The current report constitutes a first formal observation of this kind of tautomerism observed in spiro-indoline pyrazolines.

Entities:  

Keywords:  1,3-Dipolar Cycloaddition; Heterocycles; Indolines; Regioselectivity; Spiro-isoxazolines; Spiro-pyrazolines; Tautomerism

Year:  2014        PMID： 24882890      PMCID： PMC4036741          DOI： 10.1016/j.tetlet.2014.02.052

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


  28 in total

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Authors:  Yves L Janin
Journal:  Chem Rev       Date:  2012-05-01       Impact factor: 60.622

Review 2.  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

3.  Multicomponent synthesis of spiroisoxazolines.

Authors:  Mauro F A Adamo; Donato Donati; Eleanor F Duffy; Piero Sarti-Fantoni
Journal:  J Org Chem       Date:  2005-10-14       Impact factor: 4.354

4.  Oxonium Ion Mediated Synthesis of 4-Substituted Spiro-Isoxazolines.

Authors:  Eric McClendon; Ann O Omollo; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2009-02-04       Impact factor: 2.415

5.  A [3+2] dipolar cycloaddition route to 3-hydroxy-3-alkyl oxindoles: an approach to pyrrolidinoindoline alkaloids.

Authors:  Anand Singh; Gregory P Roth
Journal:  Org Lett       Date:  2011-03-22       Impact factor: 6.005

6.  An alkynyliodide cycloaddition strategy for the construction of iodoisoxazoles.

Authors:  James A Crossley; Duncan L Browne
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

7.  Tautomerism-dependent ring construction of N-heterocyclic compounds from the reactions of 1-alkynyl Fischer carbene complexes and substituted pyrazolinones.

Authors:  Zhaoyan Zheng; Zhengkun Yu; Ning Luo; Xiuwen Han
Journal:  J Org Chem       Date:  2006-12-22       Impact factor: 4.354

8.  Construction of Novel Spiroisoxazolines via Intramolecular Cyclization/Methylation.

Authors:  Erick D Ellis; Jianping Xu; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2009-09-30       Impact factor: 2.415

9.  A Novel Synthesis of 1,3,5-Trisubstituted Pyrazoles through a Spiro-pyrazoline Intermediate via a Tandem 1,3-Dipolar Cycloaddition/Elimination.

Authors:  Sureshbabu Dadiboyena; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2009-01-21       Impact factor: 2.415

10.  Base-mediated reaction of hydrazones and nitroolefins with a reversed regioselectivity: a novel synthesis of 1,3,4-trisubstituted pyrazoles.

Authors:  Xiaohu Deng; Neelakandha S Mani
Journal:  Org Lett       Date:  2008-02-27       Impact factor: 6.005
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  1 in total

1.  Reaction Products of β-Aminopropioamidoximes Nitrobenzenesulfochlorination: Linear and Rearranged to Spiropyrazolinium Salts with Antidiabetic Activity.

Authors:  Lyudmila Kayukova; Anna Vologzhanina; Pavel Dorovatovskii; Gulnur Baitursynova; Elmira Yergaliyeva; Ayazhan Kurmangaliyeva; Zarina Shulgau; Sergazy Adekenov; Zhanar Shaimerdenova; Kydymolla Akatan
Journal:  Molecules       Date:  2022-03-28       Impact factor: 4.411
  1 in total

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