Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

The first example of the cycloaddition of in situ-generated azomethine imine under microwave conditions is described. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones proceeds regio- and stereoselectively giving mostly good yields of the corresponding perhydrop...

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Main Authors:	Alexander P. Molchanov, Mariia M. Efremova, Mariya A. Kryukova, Mikhail A. Kuznetsov
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	azomethine imines cycloaddition diazabicyclohexanes diaziridines regioselectivity
Online Access:	https://doi.org/10.3762/bjoc.16.218

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spelling	doaj-931af78ec7d24572b598ef5c31a748762021-04-02T16:28:21ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-10-011612679268610.3762/bjoc.16.2181860-5397-16-218Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiationAlexander P. Molchanov0Mariia M. Efremova1Mariya A. Kryukova2Mikhail A. Kuznetsov3Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, RussiaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, RussiaThe first example of the cycloaddition of in situ-generated azomethine imine under microwave conditions is described. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones proceeds regio- and stereoselectively giving mostly good yields of the corresponding perhydropyrazolopyrazoles. The products of the reaction undergo cycloreversion under the reaction conditions.https://doi.org/10.3762/bjoc.16.218azomethine iminescycloadditiondiazabicyclohexanesdiaziridinesregioselectivity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Alexander P. Molchanov Mariia M. Efremova Mariya A. Kryukova Mikhail A. Kuznetsov
spellingShingle	Alexander P. Molchanov Mariia M. Efremova Mariya A. Kryukova Mikhail A. Kuznetsov Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation Beilstein Journal of Organic Chemistry azomethine imines cycloaddition diazabicyclohexanes diaziridines regioselectivity
author_facet	Alexander P. Molchanov Mariia M. Efremova Mariya A. Kryukova Mikhail A. Kuznetsov
author_sort	Alexander P. Molchanov
title	Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation
title_short	Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation
title_full	Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation
title_fullStr	Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation
title_full_unstemmed	Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation
title_sort	selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-10-01
description	The first example of the cycloaddition of in situ-generated azomethine imine under microwave conditions is described. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones proceeds regio- and stereoselectively giving mostly good yields of the corresponding perhydropyrazolopyrazoles. The products of the reaction undergo cycloreversion under the reaction conditions.
topic	azomethine imines cycloaddition diazabicyclohexanes diaziridines regioselectivity
url	https://doi.org/10.3762/bjoc.16.218
work_keys_str_mv	AT alexanderpmolchanov selectiveandreversible13dipolarcycloadditionof6aryl15diazabicyclo310hexaneswith13diphenylprop2en1onesundermicrowaveirradiation AT mariiamefremova selectiveandreversible13dipolarcycloadditionof6aryl15diazabicyclo310hexaneswith13diphenylprop2en1onesundermicrowaveirradiation AT mariyaakryukova selectiveandreversible13dipolarcycloadditionof6aryl15diazabicyclo310hexaneswith13diphenylprop2en1onesundermicrowaveirradiation AT mikhailakuznetsov selectiveandreversible13dipolarcycloadditionof6aryl15diazabicyclo310hexaneswith13diphenylprop2en1onesundermicrowaveirradiation
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Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

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