The preparation of 2-hydroxyethyl-2,3-dihydro-2H-1,4-benzoxazin-3(4H)- one derivatives

Synthetic Communications

Volumn 28, Issue 18, 1998, Pages 3471-3478

  Frechette, Roger F ^a   Beach, Michael J ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYETHYL 2,3 DIHYDRO 2H 1,4 BENZOXAZIN 3(4H) ONE; BENZOXAZINE DERIVATIVE; GAMMA BUTYROLACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031782574     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004455     Document Type: Article

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24. Hydroxy substitution at the 2-position of the 1,4-benzoxazinone nucleus with 0, 1 and 3-carbon spacers have been reported: (a) Sicker, D.; Hartenstein, H. Synthesis 1993, 771. (b) Quiroz, A.; Niemeyer, H. M. Heterocycles 1991, 32, 1681. (c) Bartsch, H.; Schwarz, O. J. Heterocycl. Chem. 1982, 19, 1189.
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27. (b) The nmr spectrum of the intermediate hydroxy acid was consistent with the structure. The structure was not rigorously proved, except by reconversion to the phenoxyfuranone derivative.
28. In all cases, the products obtained after the crude workup were sufficiently pure to carry on as synthetic intermediates. Analytically pure material could be isolated after a single crystallization or trituration step. Yields shown reflect product obtained after purification at each step with, typically, only one crop collected following a crystallization or trituration procedure. Also, with the exception of the parent system ring (ie., 2a), product yields were the result of a single trial.
29. Details of the structure activity relationships will be available in a manuscript which is in preparation.