| Autor: |
Pozharskii AF; Department of Organic Chemistry , Southern Federal University , Zorge str 7 , 344090 Rostov-on-Don , Russian Federation., Ozeryanskii VA; Department of Organic Chemistry , Southern Federal University , Zorge str 7 , 344090 Rostov-on-Don , Russian Federation., Dyablo OV; Department of Organic Chemistry , Southern Federal University , Zorge str 7 , 344090 Rostov-on-Don , Russian Federation., Pogosova OG; Department of Organic Chemistry , Southern Federal University , Zorge str 7 , 344090 Rostov-on-Don , Russian Federation., Borodkin GS; Institute of Physical and Organic Chemistry , Southern Federal University , Stachki Ave 194/2 , 344090 Rostov-on-Don , Russian Federation., Filarowski A; Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-383 Wroclaw, Poland and Institute of Chemistry , St. Petersburg State University , Universitetskij pr 26 , 198504 St. Petersburg , Russian Federation. |
| Abstrakt: |
It has been found that 1-dialkylamino-8-(pyrrolyl-1)naphthalenes 1 and 6, upon treatment with an equimolar amount of HBF 4 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. |
