Synthesis of new methine class of dyes bearing maleimide ring system

Yoshinori Tominaga, Kaori Komiya, Sachiko Itonaga, Noriko Yoshioka, Seigo Kataoka, Kenji Sasaki, Takashi Hirota

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Reaction of l-methyl-3-methylthiomaleimides (1a-c) with N,N-dialkylanilines (2) under refluxing in acetic acid condition gave the corresponding 3-(4-diakylamino)phenyl-1-methylmaleimides (3a-g). Treatment of these 1-methyl-3-phenylmaleimides (3a, c) with Lawesson's reagent under refluxing in toluene afforded new blue dyes, 4-(4-dialkylamino)phenyl-3-cyano-1-methyl-5-oxopyrrole-2-thiones (5a, b) which are brilliant blue dyes appearing at 606 and 615 nm (log ε: 4.59 and 4.50) in UV spectra. Reaction of 4-methoxycarbonyl-1-methyl-3-methylthiomaleimide (1b) with 3-dialkylamino-phenol under the same reaction conditions gave cyclizcd products, 2H, 4H-[1]-benzopyrano[3,4-c]pyrrole-1,3,4-triones (6a-c) in good yields.

Original languageEnglish
Pages (from-to)41-44
Number of pages4
JournalHeterocycles
Volume46
Issue number1
Publication statusPublished - 1997
Externally publishedYes

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Bearings (structural)
2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Coloring Agents
Thiones
Pyrroles
Toluene
Phenol
Acetic Acid
maleimide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Tominaga, Y., Komiya, K., Itonaga, S., Yoshioka, N., Kataoka, S., Sasaki, K., & Hirota, T. (1997). Synthesis of new methine class of dyes bearing maleimide ring system. Heterocycles, 46(1), 41-44.

Synthesis of new methine class of dyes bearing maleimide ring system. / Tominaga, Yoshinori; Komiya, Kaori; Itonaga, Sachiko; Yoshioka, Noriko; Kataoka, Seigo; Sasaki, Kenji; Hirota, Takashi.

In: Heterocycles, Vol. 46, No. 1, 1997, p. 41-44.

Research output: Contribution to journalArticle

Tominaga, Y, Komiya, K, Itonaga, S, Yoshioka, N, Kataoka, S, Sasaki, K & Hirota, T 1997, 'Synthesis of new methine class of dyes bearing maleimide ring system', Heterocycles, vol. 46, no. 1, pp. 41-44.
Tominaga Y, Komiya K, Itonaga S, Yoshioka N, Kataoka S, Sasaki K et al. Synthesis of new methine class of dyes bearing maleimide ring system. Heterocycles. 1997;46(1):41-44.
Tominaga, Yoshinori ; Komiya, Kaori ; Itonaga, Sachiko ; Yoshioka, Noriko ; Kataoka, Seigo ; Sasaki, Kenji ; Hirota, Takashi. / Synthesis of new methine class of dyes bearing maleimide ring system. In: Heterocycles. 1997 ; Vol. 46, No. 1. pp. 41-44.
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AU - Tominaga, Yoshinori

AU - Komiya, Kaori

AU - Itonaga, Sachiko

AU - Yoshioka, Noriko

AU - Kataoka, Seigo

AU - Sasaki, Kenji

AU - Hirota, Takashi

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N2 - Reaction of l-methyl-3-methylthiomaleimides (1a-c) with N,N-dialkylanilines (2) under refluxing in acetic acid condition gave the corresponding 3-(4-diakylamino)phenyl-1-methylmaleimides (3a-g). Treatment of these 1-methyl-3-phenylmaleimides (3a, c) with Lawesson's reagent under refluxing in toluene afforded new blue dyes, 4-(4-dialkylamino)phenyl-3-cyano-1-methyl-5-oxopyrrole-2-thiones (5a, b) which are brilliant blue dyes appearing at 606 and 615 nm (log ε: 4.59 and 4.50) in UV spectra. Reaction of 4-methoxycarbonyl-1-methyl-3-methylthiomaleimide (1b) with 3-dialkylamino-phenol under the same reaction conditions gave cyclizcd products, 2H, 4H-[1]-benzopyrano[3,4-c]pyrrole-1,3,4-triones (6a-c) in good yields.

AB - Reaction of l-methyl-3-methylthiomaleimides (1a-c) with N,N-dialkylanilines (2) under refluxing in acetic acid condition gave the corresponding 3-(4-diakylamino)phenyl-1-methylmaleimides (3a-g). Treatment of these 1-methyl-3-phenylmaleimides (3a, c) with Lawesson's reagent under refluxing in toluene afforded new blue dyes, 4-(4-dialkylamino)phenyl-3-cyano-1-methyl-5-oxopyrrole-2-thiones (5a, b) which are brilliant blue dyes appearing at 606 and 615 nm (log ε: 4.59 and 4.50) in UV spectra. Reaction of 4-methoxycarbonyl-1-methyl-3-methylthiomaleimide (1b) with 3-dialkylamino-phenol under the same reaction conditions gave cyclizcd products, 2H, 4H-[1]-benzopyrano[3,4-c]pyrrole-1,3,4-triones (6a-c) in good yields.

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