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Heterocyclic compounds. X. A new synthesis of thiadiazasteroids
Author(s) -
Manhas M. S.,
Sugiura M.,
Chawla H. P. S.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150610
Subject(s) - chemistry , levulinic acid , yield (engineering) , solvent , boiling , organic chemistry , tetra , nuclear magnetic resonance spectroscopy , medicinal chemistry , catalysis , materials science , metallurgy
The reaction of ν‐ketoacids or ν‐aldehydo acids with o ‐amino amides results in the formation of 4‐quinazolones. Using this reaction a number of polyheterosteroid analogs were synthesized. Thus, when 2‐amino‐3‐carboxamido‐4,5,6,7‐tetrahydrobenzothiophene (9) was refluxed with levulinic acid (10) in a high boiling solvent, thiadiazasteroid analog (11) was obtained in 78% yield. It was found that this facile one‐step reaction could be used to synthesize a variety of tetra and pentacyclic compounds. Nmr spectroscopy was used to assign stereochemistry to the 17‐methyl “steroids” (31) and (32).