1-Phenethyl-, 1-Styryl-および1-Isopentyl-1,2,3,4-tetrahydroisoquinoline型化合物の合成

概要

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Our previous report described nuclear magnetic resonance spectra of 1-phenethyl-and 1-styryl-1,2,3,4-tetrahydroisoquinoline derivatives. In the present series of work, these compounds (VII, VIII, XIII) were synthesized by the so-called Dobrovsky reaction and Bischler-Napieralsky reaction, followed by reduction with sodium borohydride and the application of formaldehyde and sodium borohydride. In order to assign aromatic protons at 5- and 8-positions of the isoquinoline ring in 7-hydroxy-1,2,3,4-tetrahydroisoquinoline derivatives, deuterium exchange reaction of aromatic proton was utilized but the corresponding deuterium compound of 1-styryl-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinol (Vb') could not be obtained. This compound (Vb') was found to undergo isomerisation with alkali to XIV.
公益社団法人日本薬学会の論文
1970-09-25