Naphth[1,2-d]oxazole intermediates in the preparation of 3-hydroxy-4-(1-alkyl-3-methyl-5-hydroxy-4-pyrazolyl)-azo-1-naphthalenesulfonamide dyes

Autor:	Bogumila Rachwal, Alan R. Katritzky, Terrance P. Smith, Stanislaw Rachwal, David W. Macomber
Rok vydání:	1993
Předmět:	Acylation Diethylamine chemistry.chemical_compound Benzoyl chloride Thionyl chloride chemistry Organic Chemistry Pyridine Moiety Organic chemistry Pyridinium Medicinal chemistry Oxazole
Zdroj:	Journal of Heterocyclic Chemistry. 30:135-139
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570300124
Popis:	Acylation of 4-amino-3-hydroxy-1-naphthalenesulfonic acid (3) with benzoyl chloride in pyridine gave pyridinium 3-hydroxy-4-(N-benzoylamino)-1-naphthalenesulfonate (12) which was converted by thionyl chloride followed by diethylamine into N,N-diethyl-2-phenylnaphth[1,2-d]oxazole-5-sulfonamide (14). The naphthoxazole moiety was hydrolyzed with potassium hydroxide and the resulting N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide (11) coupled with 1-alkyl-3-methyl-5-pyrazolones. The 2-phenylnaphth[1,2-d]oxazole intermediates and various by-products were investigated.
Databáze:	OpenAIRE
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