2026-04-21T11:11:28Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/49252022-12-20T11:08:25Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
1,5-O → N Carbamoyl Snieckus–Fries-Type Rearrangement
Feberero, Claudia
Suarez Pantiga, Samuel
Cabello Fernández, Zaida
Sanz Díez, Roberto
Química orgánica
Chemistry, Organic
The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus–Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.
Junta de Castilla y León and FEDER
(BU076U16) and Ministerio de Economía
y Competitividad
(MINECO) and FEDER (CTQ2016-48937-C2-1-P)
2018-09-07T10:42:31Z
2019-04-20T02:45:07Z
2018-04
info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
1523-7060
http://hdl.handle.net/10259/4925
10.1021/acs.orglett.8b00782
eng
Organic Letters. 2018, V. 20, n. 8, p. 2437–2440
https://doi.org/10.1021/acs.orglett.8b00782
info:eu-repo/grantAgreement/JCyL/BU076U16
info:eu-repo/grantAgreement/MINECO/CTQ2016-48937-C2-1-P
info:eu-repo/semantics/openAccess
application/pdf
American Chemical Society