2-vinylpyrroles and pyrrolo[3,2-d]pyrimidines from direct addition of aldehydes to 4-amino-pyrrole-2-carboxylate derivatives.
A new methodology for the direct preparation of 2-vinylpyrroles is presented. Treatment of 4-amino-pyrrole-2-carboxylates 5a-c and 6a-d with aliphatic aldehydes and TFA furnished 2-vinylpyrroles 2a-k in 9-87% yields. Under similar conditions ureidopyrroles 5a-c reacted with aryl aldehydes to provide pyrrolo[3,2-d]pyrimidines 1a-d in 28-63% yields.
Fridkin
Gil
G
Département de Chimie, Université de Montréal, C.P 6128 Succursale Centre Ville, Montréal, Québec, Canada H3C 3J7.
Lubell
William D
WD
D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D002264:Carboxylic Acids; D011743:Pyrimidines; D011758:Pyrroles; D014753:Vinyl Compounds