- A convenient synthesis of 1-substituted 1,4-dihydroisoquinolin-3-ones
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A number of isoquinolin-3-ones have been obtained in fair to good yields by reaction of phenylacetonitrile with carbonyl compounds in PPA.
- Barbry, Didier,Sokolowski, Guillaume,Champagne, Philippe
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- Superacidic activation of 1- and 3-isoquinolinols and their electrophilic reactions
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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, Konstantin Yu.,Prakash, G. K. Surya,Rasul, Golam,Olah, George A.
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p. 8943 - 8951
(2007/10/03)
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- 1-Aryl-1,4-dihydro-3(2H)-isoquinolinones: Two modes of interaction with 5-HT(1A) receptors
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Two series of 1-aryl-1,4-dihydro-3(2H)-isoquinoline derivatives were synthesized, and their in vitro and in vivo properties at 5-HT(1A) and 5- HT(2A) receptors were evaluated. In was shown that series a, containing a 1- (m-chlophenyl)piperazine fragment, interacts with 5-HT(1A) receptors in two different modes: as an ordinary 4-substituted 1-arylpiperazine and as a pseudo one. Series b, with a 1,2,3,4-tetrahydroisoquinoline moiety, binds to the receptor thanks to a pseudo 1-arylpiperazine fragment. Regardless of the mode of interaction, both those series demonstrated 5-HT(1A) receptor antagonistic properties in animal models. Different in vivo properties of 2b, due to a 7-methoxy substituent, indicate that the isoquinolinone portion also interacts with 5-HT(1A) receptors.
- Mokrosz,Duszynska,Wesolowska,Borycz,Chojnacka-Wojcik,Karolak-Wojciechowska
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- Novel Routes to 1-Aryl-1,4-dihydro-3(2H)-isoquinolinones and 2-Substituted or 2,3-Disubstituted Benzofurans by Intramolecular Cyclizations
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N-(α-Benzotriazolylalkyl)arylacetamides, readily available from an arylacetamide, an aldehyde and benzotriazole, undergo intramolecular cyclization under acidic conditions to give 1-aryl-1,4-dihydro-3(2H)-isoquinolinones in good to excellent yields.Similarly, 2-(benzotriazol-1-yl)-2-(o-hydroxyphenyl)ethanols, obtained by lithiation of 2-(benzotriazol-1-ylmethyl)phenols followed by quenching with aldehydes or ketones, eliminate a molecule of water and a molecule of benzotriazole yielding 2-substituted and 2,3-disubstituted benzofurans.
- Katritzky, Alan R.,Lan, Xiangfu,Zhang, Zhongxing
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p. 381 - 387
(2007/10/02)
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