Coupling of two diazotized 3-aminothieno[3,4-c]coumarins with aromatic amines

Emmanuel Sopbué Fondjo, Joseph Tsemeugne, Beibam Luc Sondengam, Thomas Oppenlaender, Hippolyte Kamdem Wabo, Pierre Tane, Joseph D. Connolly, Wim Dehaen, Taoufik Rohand, Haruhisa Kikuchi, Yoshiteru Oshima

研究成果: Article査読

5 被引用数 (Scopus)

抄録

The coupling reactions of two diazotized 3-aminothieno[3,4-c]coumarins were investigated. Compounds 1a,b both react with sodium nitrite in concentrated sulphuric acid at 0-5°C to give the diazotized intermediates 2 and 3, the latter resulting from the acid-catalyzed hydrolysis of the lactonic ring of 2. The in situ formed diazonium salts react with aromatic amines (4) to afford a series of arylazothiophenes dyes in the form of their ammonium sulfate salts. With diazotized aniline, besides the normally expected phenylazothiophene 10 from the reaction with compound 1a, the corresponding product of acid hydrolysis 11 was also isolated. In at least one of the cases, the thienyl diazonium salt 2 undergoes a Gomberg-Bachmann arylation reaction with p-nitroaniline to give the 2-arylthiophene 9. The direct hydrolysis of compounds 1a,b by concentrated sulphuric acid and subsequent oxidative dimerization of the primary product of acid hydrolysis led to compound 12.

本文言語English
ページ(範囲)1295-1301
ページ数7
ジャーナルJournal of Heterocyclic Chemistry
48
6
DOI
出版ステータスPublished - 2011 11月

ASJC Scopus subject areas

  • 有機化学

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