Chemistry of Heterocyclic Compounds p. 1084 - 1088 (1981)
Update date:2022-08-03
Topics: Amines Hydrolysis Intramolecular hydrogen bond Electronic spectra Bathochromic shift Piperidine Hydroxy group Elementary analysis Spectral properties
Panfilova, E. A.
Kvitko, I. Ya.
El'tsov, A. V.
The reaction of 1-methyl-2,5-dichloro-3,4-diformylpyrrole with amines of the aliphatic series leads to products of replacemant of one chlorine atom.With aromatic amines the reaction takes place at one of the formyl groups to give aminals.The latter in the presence of excess amine readily give bisazomethines of 1-methyl-2-chloro-5-arylamino-3,4-diformylpyrrole,wich can also be obtained directly by the reaction of dichlorodiformylpyrrole with aryl amines.It is shown that in this case one of the formyl groups and the adjacent chlorine atom react initially,after wich thesecond formyl group reacts.The chlorine atom in bisazomethines of 1-methyl-2-chloro-5-arylamino-3,4-diformylpyrrole has high nucleophilic lability and is easily replaced by a hydroxy group or a piperidine residue.
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Doi:10.1007/BF00506989
(1981)Doi:10.1021/om0400954
(2004)Doi:10.1021/ja00373a027
(1982)Doi:10.1016/j.tet.2004.09.029
(2004)Doi:10.1021/ja00372a037
(1982)Doi:10.1246/bcsj.77.1915
(2004)
