Thiazole analogs of benzomorphans. I. Synthesis of novel thiazolo[4,5-f]morphans

DOI: 10.1248/cpb.30.4378

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 4378 - 4383 (1982)

Update date:2022-08-10

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Authors:

Katsuura

Ohta Ohta

Mitsuhashi

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Article abstract of DOI:10.1248/cpb.30.4378

The synthesis and analgesic properties of thiazolo[4,5-f]morphans (XIIa-c) are described. Monothiazolization of ethyl 2-methyl-1,3-dioxo-2-cyclohexaneacetate (I) afforded the 2-aminothiazole derivative (II), which was deaminated to ethyl 4,5,6,7-tetrahydro-4-methyl-5-oxo-4-benzothiazoleacetate (V) by means of the Sandmeyer reaction and subsequent hydrogenolysis of the resulting chloride (IVa). In several steps, V was converted to 2,5-dimethyl-9-oxothiazolo[4,5-f]morphan (X). Thiazolo[4,5-f]morphan derivatives (XIIa-c) were synthesized from this key intermediate (X).

Full text of DOI:10.1248/cpb.30.4378

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