Issue 16, 1970

An aryne route to laureline, and related topics

Abstract

A route to laureline (IX), involving as key steps treatment of 1-(3-bromo-4-methoxybenzyl)-1,2,3,4-tetrahydro-2-methyl-6,7-methylenedioxyisoquinoline (IIa) with potassamide in liquid ammonia followed by Pschorr ringclosure, is described, together with details of the synthesis of compound (IIa) and related compounds from the appropriate phenethylamines and 3-bromo-4-methoxyphenylacetic acid.

The problem of polymerisation which supervenes in amine-catalysed condensation of aromatic aldehydes with nitromethane contaminated with methyl nitrite is noted.

Article information

Article type
Paper

J. Chem. Soc. C, 1970, 2234-2238

An aryne route to laureline, and related topics

M. S. Gibson, G. W. Prenton and J. M. Walthew, J. Chem. Soc. C, 1970, 2234 DOI: 10.1039/J39700002234

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