106944-17-6Relevant articles and documents
Etude des proprietes enaminiques de l'amino-3 thiophene et du diamino-3,4 thiophene
Outurquin, Francis,Lerouge, Patrice,Paulmier, Claude
, p. 267 - 275 (2007/10/02)
In the preceding paper, access to secondary and tertiary amines derived from 3-aminothiophene 1a and 3,4-diaminothiophene 3a has been discussed (1).Our results concerning the enamine character of these thiophenic amines are presented here.Using acidic catalysis, α-deuteration of the amines 1a to 1d and α,α'-dideuteration of diamine 3a have been observed.The C-protonation of 1a explains the formation of the bis(thienyl-3)amine 5 through a transamination reaction.Bromination leads to the bromoamines 7a and 9a and α-phenylselenenylation to the phenylselenoamines 7b and 9b.The reactivity of ethyl oxomalonate toward the enamine carbons of 1a and 3a has been shown by the isolation of the aminohydroxydiesters 12 and 14.The adducts 16 and 17 have been observed in the reaction between amines 1 and ethyl pyruvate. 6-methyl 5-oxo 5H-thienopyrazine 19 is the result of the same reaction with the diamine 3a.The reductive acid-catalyzed C-alkylation of 1a and 3a, by means of an aldehyde or a ketone and two equivalents of selenophenol, allows access to 2-alkyl 3-aminothiophenes 22 and 2,5-dialkyl 3,4-diaminothiophenes 24 or to acetamides 23 and 25.
