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Nucleophilic Substitution of Hydrogen Atom in Initially Inactivated Pyrrole Ring
Alexander F Pozharskii1, Valery A Ozeryanskii1, Olga V Dyablo1
1Department of Organic Chemistry , Southern Federal University , Zorge str 7 , 344090 Rostov-on-Don , Russian Federation.
Abstract:
It has been found that 1-dialkylamino-8-(pyrrolyl-1)naphthalenes 1 and 6, upon treatment with an equimolar amount of HBF4 under ambient conditions, produce 1-dialkylammonium salts which are transformed into 7,7-dialkyl-7 H-pyrrolo[1,2- a]perimidine-7-ium tetrafluoroborates 5 and 7, respectively. The reaction proceeds in a highly selective manner and represents the first case of nucleophilic substitution of hydrogen in the initially inactivated pyrrole ring. The scope and limitations of the transformation, apparently operating due to the joint action of the "proximity effect" and proton catalysis, are outlined.
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