Solid phase synthesis of benzothiazole and thiophene derivatives based on resin-bound cyclic malonic acid ester
โ Scribed by Xian Huang; Jing Tang
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 308 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
A new method for the solid phase synthesis of benzothiazoles and 2-arylamino-3-carboxyl-4-hydroxy-5-arylthiophenes is described. Resin bound cyclic malonic acid ester was reacted with aryl isothiocyanates and then with bromine or a-bromoketones, followed by treatment with perchloric acid or sodium methoxide to afford substituted 2-methylbenzothiazoles or 2-arylamino-3-carboxyl-4-hydroxy-5-arylthiophenes, respectively, in high yields and purities.
๐ SIMILAR VOLUMES
A resin-bound cyclic malonic ester has been prepared on Merrifield resin. Reaction of the cyclic malonic ester with triethyl orthoformate and subsequent substitution by an arylamine afforded arylaminomethylene cyclic malonic ester preloaded resin. A series of 4(1H)quinolones were prepared by thermal
Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to a-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres.