DBU-mediated [4 + 1] annulations of donor-acceptor cyclopropanes with carbon disulfide or thiourea for synthesis of 2-aminothiophene-3-carboxylates.
Org Biomol Chem
; 15(37): 7878-7886, 2017 Sep 26.
Article
em En
| MEDLINE
| ID: mdl-28891577
ABSTRACT
DBU-mediated [4 + 1] annulations of donor-acceptor cyclopropanes with carbon disulfide or thiourea to form 2-aminothiophene-3-carboxylate derivatives have been discovered. This reaction proceeds via the ring opening of donor-acceptor cyclopropanes to produce a 2-(iminomethylene)but-3-enoate intermediate, followed by the attack of an S-nucleophile for regioselective intermolecular nucleophilic addition, intramolecular S-nucleophilic addition, and final aromatization. A variety of functional groups could be tolerated under the reaction conditions.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Tioureia
/
Dissulfeto de Carbono
/
Ácidos Carboxílicos
/
Compostos Bicíclicos Heterocíclicos com Pontes
/
Ciclopropanos
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article