Cleavage of some annulated tetrahydropyridines under the action of dimethyl acetylene dicarboxylate in protic solvents. New practical route to substituted pyrroles and indoles.
Tetrahydropyrrolo[3,2-c]pyridines and tetrahydropyrido[4,3-b]indoles undergo piperidine ring opening under the action of dimethyl acetylene dicarboxylate in alcohols or in aqueous dioxane, providing beta-(alk)oxy-substituted pyrroles (indoles) in moderate to high yields.
Borisova
Tatiana N
TN
Organic Chemistry Department, Russian Peoples Friendship University, 6, Miklukho-Maklaya St., Moscow 117198, Russia.
Voskressensky
Leonid G
LG
Soklakova
Tatiana A
TA
Kulikova
Larisa N
LN
Varlamov
Alexey V
AV
D000114:Acetylene / Q000494:pharmacology*; D000438:Alcohols / Q000737:chemistry; D002264:Carboxylic Acids / Q000494:pharmacology*; D004146:Dioxanes / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry* / Q000378:metabolism*; D011758:Pyrroles / Q000737:chemistry; D012997:Solvents
D000438:Alcohols; D002264:Carboxylic Acids; D004146:Dioxanes; D007211:Indoles; D010880:Piperidines; D011725:Pyridines; D011758:Pyrroles; D012997:Solvents; C032727:piperidine; C025223:1,4-dioxane; D000114:Acetylene