Synthesis of 1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-11b-methyl [1,4]thiazino[3,4-a]isoquinoline derivatives

Autor:	I. Jirkovsky, R. Noureldin
Rok vydání:	1980
Předmět:	chemistry.chemical_compound Chemistry Yield (chemistry) Organic Chemistry Periodate Organic chemistry Sulfoxide Alkylation Isoquinoline Nmr data Diborane
Zdroj:	Journal of Heterocyclic Chemistry. 17:449-453
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570170307
Popis:	Alkylation of the 2-mercaptoacetamide 4a with chloropropanone afforded the ketoamide 10 which on direct acid-catalyzed cyclization furnished 12. The cyclization can be arrested at the stage of the enamide 11. Periodate oxidation of 12 gave the equatorial sulfoxide 14. Reduction of 12 with diborane led to 13 which was oxidized to yield a mixture of sulfoxides 17 and 18. The configuration of 12, 14, 17, and 18 was established on the basis of nmr data. Compounds 12, 14, and 18 showed an interesting degree of antihypertensive activity.
Databáze:	OpenAIRE
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