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11.17.1.5.2.5 Method 5: From (Ethoxycarbonylmethyl)imidodithiocarbonate or Ethyl {[1-(Methylsulfanyl)alkylidene]amino}acetates

DOI: 10.1055/sos-SD-011-00783

Kikelj, D.; Urleb, U.Science of Synthesis, (200211690.

A cyclocondensation between dimethyl (ethoxycarbonylmethyl)imidodithiocarbonate (238, R1=SMe) and carbon disulfide, followed by alkylation in situ of the intermediate 4-(ethoxycarbonyl)-2-(methylsulfanyl)thiazole-5-thiolate with alkyl halides, affords ethyl 2,5-bis(alkylsulfanyl)thiazole-4-carboxylates 239 (Scheme 89).[‌497‌,‌498‌] Similarly, cyclocondensations between α-metalated derivatives of 238 (R1=SMe) and aryl or alkyl isothiocyanates give ethyl 5-(alkyl/arylamino)-2-(methylsulfanyl)thiazole-4-carboxylates 239.[‌499‌] Ethyl 5-alkyl/aryl-2-(methylsulfanyl)thiazole-4-carboxylates 239 (R1=alkyl, aryl) are obtained from the reactions of metalated derivatives of 238 (R1=alkyl or aryl) with dithioesters.[‌500‌] Substituted ethyl thiazole-4-carboxylates with or without a substituent at position 2, are easily synthesized by analogous reactions of ethyl {[1-(methylsulfanyl)ethylene]amino} acetate with O-alkyl carbothioates in the presence of a base.[‌501‌,‌502‌]

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References


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