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Volumn , Issue 10, 2006, Pages 1599-1612

Beckmann rearrangement using indium(III) chloride: Synthesis of substituted oxazoloquinolines from the corresponding ketoximes of 3-acyl-1H-quinolin-4-ones

Author keywords

hydroxy ketoxime; Beckmann rearrangement; Cyclization; Indium(III) chloride; Oxazoloquinoline

Indexed keywords

HYDROXYLATION; INDIUM COMPOUNDS; IONS; SYNTHESIS (CHEMICAL);

EID: 33744493992     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926463     Document Type: Article
Times cited : (14)

References (48)
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    • Functional Group Transformations via Carbonyl Derivatives, Trost, B. M., Ed.; Pergamon Press: Oxford
    • (a) Maruoka, K.; Yamamoto, H. Functional Group Transformations via Carbonyl Derivatives, In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991, 763-793.
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    • note
    • We could not reproduce the result claimed by Barman et al. in ref. 11a. When the same substrate, o-hydroxyacetophenone ketoxime, was subjected to the reaction conditions described therein, a mixture of benzoxazole (68%), benzisooxazole (6%), and 2-hydroxy acetanilide (20%) were obtained within 2 hours. However, 2-hydroxyacetanilide, prepared separately, was converted only sluggishly to benzoxazole (47%) under the same reaction condition in 30 hours. Additionally, 3-chloro- and 3,5-dichloro-2-hydroxy acetophenone ketoxime resulted in a mixture of the corresponding benzoxazole (81% and 73%) and benzisooxazole (7% and 8%) respectively without any corresponding acetanilide.
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    • note
    • X-ray crystal structure analysis of 2e and 3i: atomic coordinates, bond lengths [Å] and angles [deg], anisotropic displacement parameters, hydrogen coordinates, torsion angles [deg] have been deposited at Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, under deposition number CCDC 273870 for 2e, CCDC 273871 for 3i [fax: +44(1223)336033], E-mail: deposit@ccdc.cam.ac.uk). 1613-1624


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.