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15.5.1 Product Subclass 1: Isoquinolines

DOI: 10.1055/sos-SD-015-01146

Álvarez, M.; Joule, J. A.Science of Synthesis, (200515661.

General Introduction

Isoquinoline, a sweet-smelling, low-melting solid (mp 27°C) was first obtained in 1885 by careful separation from quinoline derived from coal tar and, once its constitution was established by oxidation to a mixture of phthalic acid and pyridine-3,4-dicarboxylic acid, named isoquinoline,[‌1‌,‌2‌] quinoline having been isolated, structurally identified, and named some thirty years earlier. The isoquinoline nucleus occurs, mainly at the 1,2,3,4-tetrahydro-level, in a large number of alkaloids;[‌3‌‌9‌] the opium poppy alkaloids papaverine (1) and, in more elaborated form, morphine (2) are examples. Emetine (3), with two tetrahydroisoquinoline units, is an amebicide (Scheme 1).

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