Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes

We developed an economical and practical protocol for the synthesis of 1,4,5,6-tetrahydropyridazines. A diverse range of alkoxyallenes and 1,2-diaza-1,3-dienes undergo (4 + 2) cycloaddition to generate the desired products in excellent yields. The high efficiency, wide substrate scope and good funct...

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Detalles Bibliográficos
Autores principales: Wu, Qi, Shao, Pan-Lin, He, Yun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9066181/
https://www.ncbi.nlm.nih.gov/pubmed/35521294
http://dx.doi.org/10.1039/c9ra02712b
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author Wu, Qi
Shao, Pan-Lin
He, Yun
author_facet Wu, Qi
Shao, Pan-Lin
He, Yun
author_sort Wu, Qi
collection PubMed
description We developed an economical and practical protocol for the synthesis of 1,4,5,6-tetrahydropyridazines. A diverse range of alkoxyallenes and 1,2-diaza-1,3-dienes undergo (4 + 2) cycloaddition to generate the desired products in excellent yields. The high efficiency, wide substrate scope and good functional group tolerance of this process, coupled with operational simplicity, render the method synthetically attractive. The utility of the cycloaddition is also demonstrated by the preparation of various pyridazines from 1,4,5,6-tetrahydropyridazines.
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spelling pubmed-90661812022-05-04 Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes Wu, Qi Shao, Pan-Lin He, Yun RSC Adv Chemistry We developed an economical and practical protocol for the synthesis of 1,4,5,6-tetrahydropyridazines. A diverse range of alkoxyallenes and 1,2-diaza-1,3-dienes undergo (4 + 2) cycloaddition to generate the desired products in excellent yields. The high efficiency, wide substrate scope and good functional group tolerance of this process, coupled with operational simplicity, render the method synthetically attractive. The utility of the cycloaddition is also demonstrated by the preparation of various pyridazines from 1,4,5,6-tetrahydropyridazines. The Royal Society of Chemistry 2019-07-10 /pmc/articles/PMC9066181/ /pubmed/35521294 http://dx.doi.org/10.1039/c9ra02712b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wu, Qi
Shao, Pan-Lin
He, Yun
Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
title Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
title_full Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
title_fullStr Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
title_full_unstemmed Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
title_short Synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
title_sort synthesis of 1,4,5,6-tetrahydropyridazines and pyridazines via transition-metal-free (4 + 2) cycloaddition of alkoxyallenes with 1,2-diaza-1,3-dienes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9066181/
https://www.ncbi.nlm.nih.gov/pubmed/35521294
http://dx.doi.org/10.1039/c9ra02712b
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