- 【Updated on May 12, 2025】 Integration of CiNii Dissertations and CiNii Books into CiNii Research
- Trial version of CiNii Research Automatic Translation feature is available on CiNii Labs
- Suspension and deletion of data provided by Nikkei BP
- Regarding the recording of “Research Data” and “Evidence Data”
Studies on Uricosuric Diuretics. V. Convenient and Efficient Synthesis of 2,3-Dihydrobenzofuran Derivatives.
Search this article
Description
A practical procedure for synthesis of a new uricosuric agent, 5-chloro-7, 8-dihydro-3-phenylfuro[2, 3-g]-1, 2-benzisoxazole-7-carboxylic acid (1, AA-193) is described, which starts from 2, 5-dichlorophenol (3b) and involves 5-chloro-6-hydroxy-3-phenyl-1, 2-benzisoxazole (2) as the key intermediate. Successive treatment of 3b with benzoyl chloride-aluminum chloride (AlCl3) and hot ethanolic sodium hydroxide gives 4-benzoyl-2, 5-dichlorophenol (8, 61%), which is oximated with hydroxylamine hydrochloride and then transformed into the benzisoxazole 2 (88%) with potassium hydroxide in N, N-dimethylformamide (DMF) (method C). The reaction of 2 with aqueous formaldehyde and dimethylamine affords the Mannich base 11a (97%), which is treated with a sulfonium ylide 12, 14 or 15 followed by heating with sodium hydroxide (NaOH) in ethanol (EtOH) to give 1 in high yield (method E).
Journal
-
- Chemical and Pharmaceutical Bulletin
-
Chemical and Pharmaceutical Bulletin 40 (10), 2597-2601, 1992
The Pharmaceutical Society of Japan
- Tweet
Keywords
Details 詳細情報について
-
- CRID
- 1390001204161007360
-
- NII Article ID
- 130003772438
-
- ISSN
- 13475223
- 00092363
-
- Text Lang
- en
-
- Data Source
-
- JaLC
- Crossref
- CiNii Articles
-
- Abstract License Flag
- Disallowed