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Quinazolines and 1,4‐benzodiazepines LVII . 1 H ‐1,4‐benzodiazepines
Author(s) -
Fryer R. Ian,
Coffen D. L.,
Earley J. V.,
Walser A.
Publication year - 1973
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.5570100410
Subject(s) - chemistry , enamine , dimethyl acetylenedicarboxylate , derivative (finance) , medicinal chemistry , double bond , organic chemistry , cycloaddition , catalysis , financial economics , economics
The preparation of the title compounds 3 and 4 using two different methods of synthesis is described. These compounds are readily reduced to 2,3‐dihydro‐1 H ‐derivatives 5 . Oxidation of 2‐alkylthio‐1 H ‐1,4‐benzodiazepines leads to the corresponding sulfoxides and sulfones. The oxidative rearrangement of sulfones 9 to a 2 H ‐1,4‐benzodiazepin‐2‐one derivative 10 is also given. The “normal” addition of azodicarboxylate together with an unusual addition of two moles of acetylenedicarboxylate to the enamine double bond of 1 H compounds is discussed.
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