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 language | English |
|---|---|
| Pages (from-to) | 41-44 |
| Number of pages | 4 |
| Journal | Heterocycles |
| Volume | 46 |
| Issue number | 1 |
| Publication status | Published - 1997 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
T1 - Synthesis of new methine class of dyes bearing maleimide ring system
AU - Tominaga, Yoshinori
AU - Komiya, Kaori
AU - Itonaga, Sachiko
AU - Yoshioka, Noriko
AU - Kataoka, Seigo
AU - Sasaki, Kenji
AU - Hirota, Takashi
PY - 1997
Y1 - 1997
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.
UR - http://www.scopus.com/inward/record.url?scp=0002129261&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0002129261&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0002129261
VL - 46
SP - 41
EP - 44
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 1
ER -