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Volumn 71, Issue 24, 2006, Pages 9217-9220

Rapid approach to 3,5-disubstituted 1,4-benzodiazepines via the photo-fries rearrangement of anilides

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; CONFORMATIONS; MICROWAVES; NEUROLOGY; PHOTOCHEMICAL REACTIONS; SUBSTITUTION REACTIONS;

EID: 33751582707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0614442     Document Type: Article
Times cited : (36)

References (46)
  • 22
    • 84944049079 scopus 로고    scopus 로고
    • See also: Katritzy, A. R., Rees, C. W., Eds.; Elsevier: Amsterdam
    • See also: Tucker, H.; Le Count, D. J. In Comprehensive Heterocyclic Chemistry II; Katritzy, A. R., Rees, C. W., Eds.; Elsevier: Amsterdam, 1996: Vol. 9, p 151.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.9 , pp. 151
    • Tucker, H.1    Le Count, D.J.2
  • 42
    • 33751556078 scopus 로고    scopus 로고
    • note
    • Different amounts of the starting material were always observed at the end of the photo-Fries rearrangement. An increase of the reaction times gave degradation of the starting material without increasing the formation of the acetophenone. The yields reported (average 45-60%) are calculated without considering the recovery of the starting material that would push yields to an average of 65-80%.
  • 43
    • 33751570789 scopus 로고    scopus 로고
    • note
    • Use of other coupling agents such as EDC, PyBOP, or DMTMM gave poor conversion into the required amides.
  • 45
    • 33751557344 scopus 로고    scopus 로고
    • note
    • This reaction was carried out inside a Discover monomode MW system from CEM. During the preparation of products 39 and 43, the formation of 10% of the corresponding 1,4-benzodiazepan-2-one was observed.
  • 46
    • 33751567602 scopus 로고    scopus 로고
    • note
    • When aminophenone 27 (as an oil), kept in a glass flask at room temperature for a long time (1 month), was used in the coupling with alanine to give amidophenone 31, we noticed the formation of a mixture of diastereoisomers (approximately 3:1), suggesting that 27 racemizes on standing.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.