A simple synthesis of 4-substituted 2,3-benzoxazinones from C-2 arylated 1,3-indanediones

Tetrahedron Letters

Volumn 52, Issue 25, 2011, Pages 3243-3246

  Das, Suven ^a,b   Koley, Pradyot ^a   Pramanik, Animesh ^a  

^a UNIVERSITY OF CALCUTTA   (India)

^b Rishi Bankim Chandra College   (India)

Author keywords

2,3 Benzoxazinones; Acid catalyzed reaction; Hydroxylamine; Ninhydrin

Indexed keywords

1,3 INDANDIONE DERIVATIVE; 4 SUBSTITUTED 2,3 BENZOXAZINONE DERIVATIVE; BENZOXAZINONE DERIVATIVE; HYDROXYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; REACTION ANALYSIS;

EID: 79956216475     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.076     Document Type: Article

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31. General procedure for the preparation of benzoxazinones 4a-f: The appropriate substrate 2a-f (1.4 mmol) was added to ethanol (15 ml) followed by the addition of hydroxylamine hydrochloride (650 mg, 9.4 mmol). The reaction mixture was refluxed for about 3 h. The cold reaction mixture was then poured into 50-60 ml ice cold water. The solid product separated was filtered and washed with water. The resulting solids were purified by crystallization from acetone to give pure products 4a-f.
32. 4: C, 58.11; H, 3.35; N, 8.47. Found: C, 58.04; H, 3.30; N, 8.42.
33. Crystallographic data for the structure 4b in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 809903. Copies of the data can be obtained, free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 01223 336033 or e-mail: deposit@ccdc.cam.ac.uk ).