Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction

An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with α-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a]indolone in moderate t...

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Detalles Bibliográficos
Autores principales: Ni, Qijian, Song, Xiaoxiao, Xiong, Jiawen, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4612130/
https://www.ncbi.nlm.nih.gov/pubmed/25476422
http://dx.doi.org/10.1039/c4cc08594a
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author Ni, Qijian
Song, Xiaoxiao
Xiong, Jiawen
Raabe, Gerhard
Enders, Dieter
author_facet Ni, Qijian
Song, Xiaoxiao
Xiong, Jiawen
Raabe, Gerhard
Enders, Dieter
author_sort Ni, Qijian
collection PubMed
description An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with α-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a]indolone in moderate to good yields (34–78%) and excellent stereoselectivities (87–99% ee, up to >20 : 1 d.r.).
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spelling pubmed-46121302015-11-09 Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction Ni, Qijian Song, Xiaoxiao Xiong, Jiawen Raabe, Gerhard Enders, Dieter Chem Commun (Camb) Chemistry An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with α-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a]indolone in moderate to good yields (34–78%) and excellent stereoselectivities (87–99% ee, up to >20 : 1 d.r.). Royal Society of Chemistry 2015-01-25 2014-12-05 /pmc/articles/PMC4612130/ /pubmed/25476422 http://dx.doi.org/10.1039/c4cc08594a Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Ni, Qijian
Song, Xiaoxiao
Xiong, Jiawen
Raabe, Gerhard
Enders, Dieter
Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
title Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
title_full Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
title_fullStr Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
title_full_unstemmed Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
title_short Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
title_sort regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an nhc-catalyzed mannich/lactamization domino reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4612130/
https://www.ncbi.nlm.nih.gov/pubmed/25476422
http://dx.doi.org/10.1039/c4cc08594a
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