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Lithiation and electrophilic substitution of 8‐chlorodibenz[ b , f ][1,4]‐oxazepine‐10‐ tert ‐butylcarbamate: The preparation of novel fused heterocyclic derivatives of 8‐chlorodibenzoxazepine
Author(s) -
Li James J.,
Chrusciel R. Alan,
Norton Monica B.,
Reitz David B.,
Hagen Timothy J.,
Tsymbalov Sofya,
Hallinan E. Ann
Publication year - 1994
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.5570310670
Subject(s) - chemistry , electrophilic substitution , yield (engineering) , electrophile , medicinal chemistry , substitution reaction , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
Lithiation of 8‐chlorodibenz[ b,f ][1,4]oxazepine‐10‐ tert ‐butylcarbamate ( 1 ) is described. Electrophilic substitution of the resulting N ‐Boc dibenzoxazepine α‐ lithioamine 2 with ketones, aldehydes, nitriles, iso‐cyanates and imines, followed by an in‐situ cyclization, gave fused carbamates 5–26 , fused 2 H ‐imidazol‐2‐ones 27–29 , fused hydantoins 30–32 , and fused ureas 33–35 , respectively, in 11–66% yield.