Complex intermediates in the NO insertion reactions into lithium amides

Nitric oxide (NO) is known to produce the carcinogenetic nitrosamines but it has also been recently reported, both as a regulator of many important physiological functions and as a possible pharmaceutical delivery system. The present paper describes the NO insertion into N - Li bond of lithium amide...

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Detalles Bibliográficos
Autor principal: Vázquez, Alvaro Joaquín
Publicado: 2006
Materias:
Hydrazones
Lithium amides
Nitrosamines
NO insertion
Tandem reactions
Chemical bonds
Drug products
Nitric oxide
Organometallics
Physiology
Reaction kinetics
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v19_n11_p748_Vazquez
http://hdl.handle.net/20.500.12110/paper_08943230_v19_n11_p748_Vazquez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_08943230_v19_n11_p748_Vazquez
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spelling paper:paper_08943230_v19_n11_p748_Vazquez2023-06-08T15:47:44Z Complex intermediates in the NO insertion reactions into lithium amides Vázquez, Alvaro Joaquín Hydrazones Lithium amides Nitrosamines NO insertion Tandem reactions Chemical bonds Drug products Nitric oxide Organometallics Physiology Reaction kinetics Hydrazones Lithium amides NO insertion Tandem reactions Nitrosamines Nitric oxide (NO) is known to produce the carcinogenetic nitrosamines but it has also been recently reported, both as a regulator of many important physiological functions and as a possible pharmaceutical delivery system. The present paper describes the NO insertion into N - Li bond of lithium amides, to afford very good to almost quantitative yields of N-nitrosamines. A study of the reaction intermediate suggested a further advantage of this synthetic methodology, widening its scope to its use in tandem reactions. Thus, in situ addition of an organolithium reagent into the N=O bond leads to an almost quantitative conversion into the corresponding hydrazone. This compound could further add a second equivalent of the same (or another) organolithium affording substituted hydrazines. The hydrazines thus prepared have a potential chiral carbon, by running the reaction in the presence of a chiral auxiliary, enantiomeric excess could be obtained. By reducing the compound with Raney Ni, the scope of this methology could be enlarged for the potential preparation of chiral primary amines, project that is currently under progress. Copyright © 2006 John Wiley & Sons, Ltd. Fil:Vázquez, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2006 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v19_n11_p748_Vazquez http://hdl.handle.net/20.500.12110/paper_08943230_v19_n11_p748_Vazquez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Hydrazones
Lithium amides
Nitrosamines
NO insertion
Tandem reactions
Chemical bonds
Drug products
Nitric oxide
Organometallics
Physiology
Reaction kinetics
Hydrazones
Lithium amides
NO insertion
Tandem reactions
Nitrosamines
spellingShingle Hydrazones
Lithium amides
Nitrosamines
NO insertion
Tandem reactions
Chemical bonds
Drug products
Nitric oxide
Organometallics
Physiology
Reaction kinetics
Hydrazones
Lithium amides
NO insertion
Tandem reactions
Nitrosamines
Vázquez, Alvaro Joaquín
Complex intermediates in the NO insertion reactions into lithium amides
topic_facet Hydrazones
Lithium amides
Nitrosamines
NO insertion
Tandem reactions
Chemical bonds
Drug products
Nitric oxide
Organometallics
Physiology
Reaction kinetics
Hydrazones
Lithium amides
NO insertion
Tandem reactions
Nitrosamines
description Nitric oxide (NO) is known to produce the carcinogenetic nitrosamines but it has also been recently reported, both as a regulator of many important physiological functions and as a possible pharmaceutical delivery system. The present paper describes the NO insertion into N - Li bond of lithium amides, to afford very good to almost quantitative yields of N-nitrosamines. A study of the reaction intermediate suggested a further advantage of this synthetic methodology, widening its scope to its use in tandem reactions. Thus, in situ addition of an organolithium reagent into the N=O bond leads to an almost quantitative conversion into the corresponding hydrazone. This compound could further add a second equivalent of the same (or another) organolithium affording substituted hydrazines. The hydrazines thus prepared have a potential chiral carbon, by running the reaction in the presence of a chiral auxiliary, enantiomeric excess could be obtained. By reducing the compound with Raney Ni, the scope of this methology could be enlarged for the potential preparation of chiral primary amines, project that is currently under progress. Copyright © 2006 John Wiley & Sons, Ltd.
author Vázquez, Alvaro Joaquín
author_facet Vázquez, Alvaro Joaquín
author_sort Vázquez, Alvaro Joaquín
title Complex intermediates in the NO insertion reactions into lithium amides
title_short Complex intermediates in the NO insertion reactions into lithium amides
title_full Complex intermediates in the NO insertion reactions into lithium amides
title_fullStr Complex intermediates in the NO insertion reactions into lithium amides
title_full_unstemmed Complex intermediates in the NO insertion reactions into lithium amides
title_sort complex intermediates in the no insertion reactions into lithium amides
publishDate 2006
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v19_n11_p748_Vazquez
http://hdl.handle.net/20.500.12110/paper_08943230_v19_n11_p748_Vazquez
work_keys_str_mv AT vazquezalvarojoaquin complexintermediatesinthenoinsertionreactionsintolithiumamides
_version_ 1768542894476492800

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