• Title/Summary/Keyword: Pummerer reaction

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A Synthesis of 1,4-Thiazine Carboxanilide: Neighboring Group Participation in Pummerer Reaction (1,4-Thiazine Carboxanilide의 합성: Pummerer 반응에서의 인접기 참여효과)

  • Han, Ho-Gyu;Nam, Gi-Dal;Ma, Hye-Deok
    • Journal of the Korean Chemical Society
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    • v.46 no.4
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    • pp.330-336
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    • 2002

  • For the purpose of development of new agrochemical fungicide of ${\alpha},{\beta}-unsaturated$ carboxanilide series a synthesis of 4-acetyl-3-methyl-N-phenyl-1,4-thiazine-2-carboxamide (6) is described. Pummerer reaction of sulfoxide 7 obtained by sulfoxidation of dihydro-1,4-thiazine methyl ester 11 gave ${\alpha}-acetoxy$ dihydro-1,4-thiazine 10a. Under the same reaction conditions, dihydro-1,4-thiazine carboxanilide sulfoxide 14 was converted to acetoxymethyl dihydro-1,4-thiazine 18 through vinylogous Pummerer reaction involving carboxanilide of sulfonium ion through intermediate 15.1,4-Thiazine carboxanilide 6 was synthesized from the treatment of ${\alpha}-acetoxy$ dihydro-1,4-thiazine 10a with acid cat-alyst followed by hydrolysis and then the reaction with aniline.

  • https://doi.org/10.5012/jkcs.2002.46.4.330 인용 PDF KSCI

Formation and Reactions of α-Phosphoryl Thiocarbocations: Synthesis of α-Sulfenyl Phosphonates

  • 김택현;오동영
    • Bulletin of the Korean Chemical Society
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    • v.16 no.7
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    • pp.609-613
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    • 1995

  • The reaction of chloro(methylthio and arylthio)methanephosphonate (1) and Pummerer-type reaction of sulfinylmethanephosphonate (2) with nucleophiles such as aromatic compounds and thiols were examined. The direct chlorination of (methylthio and arylthio)methanephosphonate with N-chlorosuccinimide (NCS) led to the formation of monochlorinated phosphonates (1) in good yield. The reaction of 1 with aromatic compounds and thiols in the presence of stannic chloride afforded a variety of aryl(methylthio)methanephosphonates (3) and thioacetals of formylphosphonates (4), respectively. Phosphonates 3 and 4 were also obtained from the reaction of Pummerer intermediate, generated from sulfinylmethanephosphonate (2), with aromatic compounds and thiols, respectively. A versatile reaction conditions to generate Pummerer intermediate were examined. The best condition was the combination of trifluoroacetic anhydride with stannic chloride. All reactions may involve an initial formation of α-phosphoryl thiocarbocation and a subsequent nucleophilic attack of aromatic compounds and thiols.

  • https://doi.org/10.5012/bkcs.1995.16.7.609 인용 PDF

Synthesis of 5-Chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2(4-methoxyphenyl)benzofuran as a $\beta-Amyloid$ Aggregation

  • Choi, Hong-Dae;Seo, Pil-Ja;Son, Byeong-Wha;Kang, Byoung-Won
    • Archives of Pharmacal Research
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    • v.26 no.12
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    • pp.985-989
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    • 2003

  • An efficient synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran (8), a potent $\beta$-amyloid aggregation inhibitor, is described. 5-Chloro-2-(4-methoxyphenyl)benzofuran (3) was obtained by the one-pot synthesis of 4-chlorophenol with $\omega$(methylsulfinyl)-p-methoxyacetophenone (1) under Pummerer reaction conditions, and it was followed by the desulfurization of the resultant 5-chloro-3-methylthio-2-(4-methoxyphenyl)benzofuran (2e). Acylation of benzofuran 3 with 4-(3-bromopropoxy)benzoyl chloride (6) gave the ketone 7, which was converted into compound 8 by the treatment of diethylamine.

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