Work

Three-Component Synthesis of 1-Substituted 5-Aminotetrazoles Promoted by Bismuth Nitrate

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A nontoxic bismuth-promoted multicomponent synthesis of 5-aminotetrazoles and bistetrazoles is reported. The reaction of phenyl isothiocyanate, NaN 3, and amine (primary aliphatic, aromatic, and aliphatic diamine) promoted by Bi(NO 3 ) 3 ·5H 2 O under microwave heating affords good yields, short reaction times, simple workup, and purification without column chromatography. A set of diagnostic 1 H NMR signals was identified as a guide for quickly elucidating the exclusive (or main) regioisomer formed, with the stronger electron donor group located at heterocyclic nitrogen 1. This regioselectivity is strongly dependent on the electronic density of the amine. It is opposite to that obtained by several thiourea desulfurization methods promoted by thiophilic metals and metal-free protocols.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01727

Authors: Iva S. de Jesus, Amenson Trindade Gomes, Igor Sande, Silvio Cunha

Institution: Universidade Federal da Bahia

Language: English

Topic: Synthesis of Tetrazole Derivatives

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação de Amparo à Pesquisa do Estado da Bahia