106944-33-6Relevant academic research and scientific papers
Acid Catalyzed α-Alkylation of β-Aminothiophenes Using Aldehydes and Selenophenol. Synthesis of Bis(3-amino-2-thienyl)methane Derivatives
Outurquin, Francis,Paulmier, Claude
, p. 5715 - 5718 (1993)
The acid-catalyzed reaction between β-aminothiophenes and aldehydes, in the presence of selenophenol, leads to α-alkyl β-aminothiophenes.The reduction step is not observed with thiophenol.Without selenol, a second alkylation reaction occurs and bis(3-amin
Acid Catalyzed α-Alkylation of β-Aminothiophenes with Aldehydes. Synthesis of 2-Alkyl 3-thiophenamines, Bis(3-amino-2-thienyl)-methane Derivatives and Dithieno[3,2-b:2′,3′-e]pyridines
Berkaoui, M'hamed,Outurquin, Francis,Paulmier, Claude
, p. 9 - 14 (2007/10/03)
The acid catalyzed reaction of 3-thiophenamines with aldehydes in the presence of selenophenol as the reducing agent, gives 2-alkyl-3-thiophenamines. Without reduction, bis(3-amino-2-thienyl)methane derivatives have been obtained and transformed into dith
N-alkylation de l'amino-3 thiophene et du diamino-3,4 thiophene
Outurquin, Francis,Lerouge, Patrice,Paulmier, Claude
, p. 259 - 266 (2007/10/02)
The stable 3-(methylamino) thiophene 2a and the 3,4-bis-(methylamino)-thiophene 16a have been prepared through the reduction of the adducts formed by the condensation of formaldehyde with the 3-aminothiophene 1 and the 3,4-diaminothiophene 13.The other se
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.
