Thiazole analogs of benzomorphans. III. Syntheses of 4,5,6,7,8,9-hexahydro-4,8-methano-5-methylthiazolo(4,5-c)azocine and 4,5,6,7,8,9-hexahydro-4,8-methano-5-methylthiazolo(5,4-c)azocine.

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Abstract
Syntheses of 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [4, 5-c] azocine (III) and 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [5, 4-c] azocine (IV) are described. Thiazolization of 2-azabicyclo [3. 3. 1] nonan-8-one (V) gave the 2-aminothiazole (VII), which was converted into III by deamination, hydrolysis of the benzoyl group and Esch-weiler-Clarke N-methylation. The 2-hydroxyl derivative (XIII) was also synthesized. On the other hand, compound (IV) was synthesized by cyclization of the olefinic urethane (XXI) with phenylselenenyl chloride, as a key step. Deselenation of XXII with triphenyltin hydride followed by LiAlH4 reduction gave IV. The urethane (XXI) was prepared from the 2-aminothiazole (XVIIa), which was obtained by condensation of the bromodiketone (XVI) and thiourea.

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