One-pot synthesis of tetrahydro-pyrrolobenzodiazepines and tetrahydro-pyrrolobenzodiazepinones through sequential 1,3-dipolar cycloaddition/ N -alkylation ( N -acylation)/Staudinger/aza-Wittig reactions

A new synthetic method for diastereoselective synthesis of tetrahydro-pyrrolo[1,2- d ][1,4]benzodiazepines and tetrahydro-pyrrolo[1,2- d ][1,4]diazepinones is developed which involves 1,3-dipolar cycloaddition, N -alkylation or N -acylation and Staudinger/aza-Wittig reactions. This one-pot and three...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (16), p.4489-4494
Main Authors: Ma, Xiaoming, Zhang, Xiaofeng, Awad, John Mark, Xie, Guoshu, Qiu, Weiqi, Zhang, Wei
Format: Article
Language:English
Subjects:
Acylation
Alkylation
Benzodiazepines
Cycloaddition
Green chemistry
Organic chemistry
Stereoselectivity
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Summary:A new synthetic method for diastereoselective synthesis of tetrahydro-pyrrolo[1,2- d ][1,4]benzodiazepines and tetrahydro-pyrrolo[1,2- d ][1,4]diazepinones is developed which involves 1,3-dipolar cycloaddition, N -alkylation or N -acylation and Staudinger/aza-Wittig reactions. This one-pot and three-step synthesis of four components gave two different heterocyclic scaffolds. Green chemistry metrics analysis of the reaction process provided favorable results.
ISSN:1463-9262
1463-9270
DOI:10.1039/C9GC01642B