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

Alan R. Katritzky, Bogumila Rachwal, Stanislaw Rachwal, David W Macomber, Terrance P. Smith

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13 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)135-139
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume30
Issue number1
DOIs
StatePublished - Jan 1 1993

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Oxazoles
Acylation
Byproducts
Coloring Agents
Acids
benzoyl chloride
potassium hydroxide
diethylamine
thionyl chloride
pyridine

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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. / Katritzky, Alan R.; Rachwal, Bogumila; Rachwal, Stanislaw; Macomber, David W; Smith, Terrance P.

In: Journal of Heterocyclic Chemistry, Vol. 30, No. 1, 01.01.1993, p. 135-139.

Research output: Contribution to journalArticle

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abstract = "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.",
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AB - 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.

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