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 | Zendy

Li James J. | Zendy; Chrusciel R. Alan | Zendy; Norton Monica B. | Zendy; Reitz David B. | Zendy; Hagen Timothy J. | Zendy; Tsymbalov Sofya | Zendy; Hallinan E. Ann | Zendy

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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.

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