Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)...

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Main Authors:	Lisa Moni, Luca Banfi, Andrea Basso, Alice Brambilla, Renata Riva
Format:	Article
Language:	English
Published:	Beilstein-Institut 2014-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	benzoxazepines diversity-oriented synthesis multicomponent reactions Mitsunobu reaction Ugi reaction
Online Access:	https://doi.org/10.3762/bjoc.10.16

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spelling	doaj-8c620b7d1a5b4cd5b9dce9d64d54fa682021-02-02T07:50:14ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-01-0110120921210.3762/bjoc.10.161860-5397-10-16Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclizationLisa Moni0Luca Banfi1Andrea Basso2Alice Brambilla3Renata Riva4Department of Chemistry and Industrial Chemistry, University of Genova, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, I-16146 Genova, ItalyDepartment of Chemistry and Industrial Chemistry, University of Genova, I-16146 Genova, ItalyAn operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic derivatives.https://doi.org/10.3762/bjoc.10.16benzoxazepinesdiversity-oriented synthesismulticomponent reactionsMitsunobu reactionUgi reaction
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Lisa Moni Luca Banfi Andrea Basso Alice Brambilla Renata Riva
spellingShingle	Lisa Moni Luca Banfi Andrea Basso Alice Brambilla Renata Riva Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization Beilstein Journal of Organic Chemistry benzoxazepines diversity-oriented synthesis multicomponent reactions Mitsunobu reaction Ugi reaction
author_facet	Lisa Moni Luca Banfi Andrea Basso Alice Brambilla Renata Riva
author_sort	Lisa Moni
title	Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_short	Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_full	Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_fullStr	Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_full_unstemmed	Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization
title_sort	diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the ugi multicomponent reaction with a mitsunobu cyclization
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2014-01-01
description	An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic derivatives.
topic	benzoxazepines diversity-oriented synthesis multicomponent reactions Mitsunobu reaction Ugi reaction
url	https://doi.org/10.3762/bjoc.10.16
work_keys_str_mv	AT lisamoni diversityorientedsynthesisofdihydrobenzoxazepinonesbycouplingtheugimulticomponentreactionwithamitsunobucyclization AT lucabanfi diversityorientedsynthesisofdihydrobenzoxazepinonesbycouplingtheugimulticomponentreactionwithamitsunobucyclization AT andreabasso diversityorientedsynthesisofdihydrobenzoxazepinonesbycouplingtheugimulticomponentreactionwithamitsunobucyclization AT alicebrambilla diversityorientedsynthesisofdihydrobenzoxazepinonesbycouplingtheugimulticomponentreactionwithamitsunobucyclization AT renatariva diversityorientedsynthesisofdihydrobenzoxazepinonesbycouplingtheugimulticomponentreactionwithamitsunobucyclization
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Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

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