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Potassamide induced in situ alkylation of 5,6-dihydroisoquinolines: Structure of products

Kasturi, Tirumalai R and Arumugam , Subramaniam and Mathew, Lata (1993) Potassamide induced in situ alkylation of 5,6-dihydroisoquinolines: Structure of products. In: Tetrahedron, 49 (11). 2345-2352 .

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Official URL: http://dx.doi.org/10.1016/S0040-4020(01)80377-X


Potassamide induced in situ alkylation of 1-alkyl- 4-cyano-3-methoxy-5,6-dihydroisoquinolines (2a & 2b) with alkyl iodides (CH3I, CH3CH2I & cyclohexyl iodide) gave the 5-alkyl- and 5,9-dialkyl-5,6-dihydroisoquinolines (4–ad & 3a–e), isoquinoline derivatives, (5a–b) and diastereomeric mixture of 4- alkyl-1,2,3,4-tetrahydroisoquinolin-3(2H)-ones (6a–e & 6′a–e). Structures were assigned on the basis of spectral data [Mass, 1H & 13C NMR, 2D NOESY & HC-COLOC]. Amide induced in situ alkylation of compounds 3a and 4a with CH3I gave in almost quantitative yield the dimethylated compounds 3d and 3a respectively. While KNH2/liq.NH3 methylation of 1,2- dihydroisoquinoline, 1 with CH3I gave the mixture of compounds, 6a & 6′a and the isoquinoline derivative 5a, NaH/benzene reaction of 1 with CH3I gave exclusively 5a. N-methylation of the mixture of compounds 6a & 6′a with NaH/CH3I gave the methylated derivatives, 7 & 8. A suitable mechanism has been proposed for the formation of products.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 23 Feb 2011 04:44
Last Modified: 23 Feb 2011 04:44
URI: http://eprints.iisc.ac.in/id/eprint/35695

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