Synthesis and Reaction of 3, 4-Diaminothiophenes

Tominaga, Yoshinori; Fujito, Hiroshi; Norisue, Hajime; Ushirogochi, Atsuyuki; Matsuda, Yoshiro; Kobayashi, Gorô

doi:10.1248/yakushi1947.99.11_1081

Cited by 18 publications

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“…The physical and spectral data of known compounds 3f, j and 4f, j were in accord with those described earlier by us 19) and Tominaga et al 15) and some data for the new compounds which were isolated are shown below. -c), (10a-c), and (12a-c).…”

Section: Methodssupporting

confidence: 84%

“…15) Typical procedure: A solution of 1-(cyanomethyl) pyridinium chloride (1, 0.10 mol), and carbon disulfide (11.4 g, 0.15 mol) in ethanol (50 ml) was treated with aqueous sodium hydroxide (10 g, 0.25 mol in 15 ml of water) under stirring in an ice bath for 20 min, and then an alkylating agent (2, 0.1 mol) was added to the reaction mixture. The resulting solution was allowed to react at room temperature for a further 4 h. The solution was then poured into ice water (300 ml) and the precipitates which separated were collected by suction and then dried.…”

Section: Methodsmentioning

confidence: 99%

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Preparation of New Nitrogen-Bridged Heterocycles 72. A New Approach to 1-Acyl-3-(substituted methylthio)thieno[3',4':4,5]imidazo[1,5-a]pyridine Derivatives

Kakehi

Suga

Okumura

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Imidazo[1,2-a]pyridine derivatives have been synthesized by several methods and shown to have a variety of pharmacological actions such as antibacterial, antifungal, antiviral, antiinflammatory, hypnotic, and antiulcer activities. [2][3][4][5][6][7][8][9][10][11][12] In contrast, imidazo[1,2-a]pyridine derivatives fused with a hetero ring at the 2-and 3-positions have been scarcely reported because of the absence of a suitable preparative method for them. We have recently described the syntheses of 3-alkylthio-1-arylcarbonyl-6,8-dimethylthieno[3Ј,4Ј:4,5]imidazo[1,2-a]pyridines 13) and 3-acyl-4-methylthio-2H-pyrano [2Ј,3Ј:4,5]imidazo[1,2-a]pyridine-2-ones.14) The former compounds were unexpectedly obtained together with 2-alkylthio-1-arylcarbonylthio-6,8-dimethylindolizine-3-carbonitriles in the alkaline treatment of 1-[1-cyano-2-(phenacylthio)vinyl]-3,5-dimethylpyridinium bromides. The plausible reaction mechanisms ( Results and DiscussionPreparation of 3-Amino-4-(1-pyridinio)thiophene-5-thiolate Derivatives We thought that the S-alkylations of 3-amino-4-(1-pyridinio)thiophene-5-thiolates with various alkylating agents should smoothly lead to the key intermediates such as D described above. Hence, the syntheses of pyridinium betaines 4a-p were investigated according to Tominaga's method. 15) However, the reactions of 1-(cyanomethyl)pyridinium chlorides (1a-c), carbon disulfide, and phenacyl bromides (2a-c) or chloroacetone (2d) in the presence of a base always afforded the mixtures of the

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Section: Methodssupporting

confidence: 84%

Section: Methodsmentioning

confidence: 99%