32637-37-9Relevant articles and documents
Synthesis and easy aromatisation of 5-substituted 6-(alkylthio)-2-methoxy-2,3-dihydropyridines. A new approach to the pyridine ring
Nedolya, Nina A.,Schlyakhtina, Nataly I.,Klyba, Lyudmila V.,Ushakov, Igor A.,Fedorov, Sergei V.,Brandsma, Lambert
, p. 9679 - 9681 (2002)
Reaction of lithiated methoxyallene, 1-ethoxyethoxyallene, 1-(methylthio)propyne and 2-butyne with methoxymethyl isothiocyanate, MeOCH2N=C=S followed by methylation affords the imidothioates H2C=C=C(R)C(SMe)=NCH2OMe [R=Me, OMe, OCH(Me)OEt, SMe]. Rearrangement to the fully conjugated systems H2C=CH-C(R)=C(SMe)-N=CHOMe and subsequent electrocyclisation of these compounds leads to the 5-substituted 6-(methylthio)-2-methoxy-2,3-dihydropyridines with good to excellent yields. In the presence of acidic catalysts or by heating at elevated temperatures these dihydropyridines eliminate methanol to afford 3-substituted 2-(methylthio)pyridines. The aroma compound 2-(methylthio)-3-pyridinol was obtained by acid-catalysed treatment of 3-(1-ethoxyethoxy)-2-(methylthio)pyridine.
Development of a new approach to generation of dihydropyridine ring: First representative of 2-alkylsulfanyl-5,6-dihydropyridin-3(4H)-ones
Nedolya,Tolmachev,Brandsma
, p. 478 - 481 (2007/10/03)
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