SIMPLE AND RAPID SYNTHESIS OF NEW SPIRO ISATIN-CYCLOPROPANE DERIVATIVES FROM 2-PYRAZOLINES

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SHAABANZADEH M.; KHABARI F.; YAVARI R.; ATAI AZIM O.

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Journal: JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY) Year:2010 | Volume:20 | Issue:76 (CHEMISTRY ISSUE) Page(s): 63-68

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Title

SIMPLE AND RAPID SYNTHESIS OF NEW SPIRO ISATIN-CYCLOPROPANE DERIVATIVES FROM 2-PYRAZOLINES

Author(s)

SHAABANZADEH M. | KHABARI F. | YAVARI R. | ATAI AZIM O. | Issue Writer Certificate

Keywords

SPIRO COMPOUNDSQ3

ISATINQ3

CYCLOPROPANEQ3

2-PYRAZOLINEQ3

LEAD TETRAACETATEQ3

Abstract

Introduction: ISATIN is a compound which has many biological effects such as antibacterial, antifungal, anti HIV and anticancer activities. The CYCLOPROPANE ring is a main structural part in many synthetic and natural compounds that exhibits many biological activities and chemists have tried to synthesis it by novel methods.Aim: In this study, a rapid and simple procedure was reported for the synthesis of new spiro ISATIN-cyclopropanes which prepared from 2-PYRAZOLINEs. These compounds have both ISATIN and CYCLOPROPANE moieties and may be of value in medicinal and pharmaceutical chemistry.Materials and Methods: The 2-PYRAZOLINEs were dissolved in toluene and then solid LEAD TETRAACETATE (LTA) was added to them at 40-50 oC and the reaction was continued for 10-20 minutes and new spiro ISATIN-cyclopropane compounds were prepared. The products were purified and their structures were deduced from their spectroscopic analysis.Results: The Kishner cyclopropanation needs higher temperatures. In this study, reaction was catalyzed with LTA and carried out in lower temperatures. One of the two resulted diastereomers was produced in higher yields than the other. For example, the diastereomeric ratio, 2a:3a=2.7:1, was determined by signal integrations in 1H NMR spectra of the mixture of compounds 2a and 3a.Conclusion: Some spiro ISATIN-cyclopropanes were synthesized in a rapid and simple procedure.

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APA: Copy

SHAABANZADEH, M., KHABARI, F., YAVARI, R., & ATAI AZIM, O.. (2010). SIMPLE AND RAPID SYNTHESIS OF NEW SPIRO ISATIN-CYCLOPROPANE DERIVATIVES FROM 2-PYRAZOLINES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), 20(76 (CHEMISTRY ISSUE)), 63-68. SID. https://sid.ir/paper/357607/en

Vancouver: Copy

SHAABANZADEH M., KHABARI F., YAVARI R., ATAI AZIM O.. SIMPLE AND RAPID SYNTHESIS OF NEW SPIRO ISATIN-CYCLOPROPANE DERIVATIVES FROM 2-PYRAZOLINES. JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY)[Internet]. 2010;20(76 (CHEMISTRY ISSUE)):63-68. Available from: https://sid.ir/paper/357607/en

IEEE: Copy

M. SHAABANZADEH, F. KHABARI, R. YAVARI, and O. ATAI AZIM, “SIMPLE AND RAPID SYNTHESIS OF NEW SPIRO ISATIN-CYCLOPROPANE DERIVATIVES FROM 2-PYRAZOLINES,” JOURNAL OF SCIENCES (ISLAMIC AZAD UNIVERSITY), vol. 20, no. 76 (CHEMISTRY ISSUE), pp. 63–68, 2010, [Online]. Available: https://sid.ir/paper/357607/en

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