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Inne
Nucleophilic substitution of hydrogen atom in initially inactivated pyrrole ring.
Autorzy
Rok wydania
2019
Czasopismo
Numer woluminu
21
Strony
1953-1957
DOI
10.1021/acs.orglett.8b04098
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Adres publiczny
https://doi.org/10.1021/acs.orglett.8b04098