Superacidic Activation of 1- and 3-Isoquinolinols and Their Electrophilic Reactions | Sciact - CRIS-system of Boreskov Institute of Catalysis

Superacidic Activation of 1- and 3-Isoquinolinols and Their Electrophilic Reactions Full article

Journal

Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904

Output data

Year: 2002, Volume: 67, Number: 25, Pages: 8943-8951 Pages count : 9 DOI: 10.1021/jo0204855

Tags

Aluminum compounds; Catalysis; Hydrogenation; Isomers

Authors

Koltunov Konstantin Yu. ¹ , Prakash G.K.Surya ¹ , Rasul Golam ¹ , Olah George A. ¹

Affiliations

1	Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California,University Park, Los Angeles, California 90089-1661

Isomeric 1- and 3-isoquinolinols (11 and 12) when activated in CF3SO3H−SbF5 acid system undergo selective ionic hydrogenation with cyclohexane to give 5,6,7,8-tetrahydro-1(2H)- and 5,6,7,8-tetrahydro-3(2H)-isoquinolinones (22 and 27). Under the influence of aluminum chloride similar products were also obtained along with 3,4-dihydro-1(2H)- and 1,4-dihydro-3(2H)-isoquinolinones (23 and 28), respectively. Compounds 11 and 12 also condense with benzene in the presence of aluminum halides, under mild conditions, to give 3,4-dihydro-3-phenyl-1(2H)- and 1,4-dihydro-1-phenyl-3(2H)-isoquinolinones (24 and 29), respectively. Prolonged reaction time or catalysis under strongly acidic HBr−AlBr3 provides an alternative reaction pathway to yield 5,6-dihydro-6,8-diphenyl-1(2H)- and 5,6,7,8-tetrahydro-6,8-diphenyl-3(2H)-isoquinolinones (25 and 30), respectively. Products 24 and 29 were also found to revert back to 11 and 12 in the presence of aluminum halides in o-dichlorobenzene. The mechanism of these intriguing reactions, which involves superelectrophilic dicationic intermediates, is discussed.

Koltunov K.Y. , Prakash G.K.S. , Rasul G. , Olah G.A.
Superacidic Activation of 1- and 3-Isoquinolinols and Their Electrophilic Reactions
Journal of Organic Chemistry. 2002. V.67. N25. P.8943-8951. DOI: 10.1021/jo0204855 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Jul 22, 2002
Published online:	Nov 19, 2002
Published print:	Dec 1, 2002

Web of science:	WOS:000179736300032
Scopus:	2-s2.0-0037073928
Elibrary:	14382403
Chemical Abstracts:	2002:874018
Chemical Abstracts (print):	138:122315
OpenAlex:	W2040101282

DB	Citing
Web of science	45
Scopus	46
OpenAlex	41