Ethyl 2-mercaptoacetate

In another example of a tandem displacement/annulation sequence, Neidlein and co-workers reported the reaction of ethyl 2-mercaptoacetate with chlorocyanopyrimidine 47 <00S255>. Thienopyrimidine 48 was produced in high yield through this one-pot procedure. 

Reaction of 3-benzenesulfonylpyrazine-2-carbonitrile with ethyl 2-mercaptoacetate and sodium carbonate gave 97% of ethyl 3-aminothieno[2,3- ]pyrazine-2-carboxylate <2006T11124>. 

The addition of a mercaptide to a nitrile provides the key reaction to the preparation of a thiazolidinone that shows diuretic activity. The hrst step in the reaction of ethyl 2-mercaptoacetate (105-2) with ethyl cyanoacetate (105-1) thus probably leads hrst to the formation of the addition product (105-3). The imino... 

Ethyl 4,5-diamino-2-(dimethylamino)thieno[2,3-z/]pyrimidine-6-carboxylate (142) was prepared in 93% yield from 4-amino-6-chloro-2-(di-methylamino)pyrimidine-5-carbonitrile (143) with ethyl 2-mercaptoacetate in refluxing EtOH-THF (5 1) (2000S255). 

The cyclic enaminones 684 condense with ethyl 2-mercaptoacetate to give the dithieno[h,/]azepines 685 and with phenylhydrazine to give the dipyrazolo[h,/]azepines Scheme 189 [89JCS(P1)2095],... 

Didecyldithieno[3,2-/ 2, 3 -d]thiophene (259) was made from tetrabro-mothiophene (254) in five steps [19]. 2,5-Dilithiation, followed by quenching with undecanal, produced 255, oxidation then giving the dione 256. Finally, ethyl 2-mercaptoacetate reacted to form the two thiophene rings. Hydrolysis and decarboxylation led to 259 (Scheme 63). 

If 3,4-dibromo-2,5-dilithiothiophene is trapped instead with ethyl chloroox-oacetate, subsequent reaction with ethyl 2-mercaptoacetate gives rise to the tetraethyl DTT-2,3,5,6-tetracarboxylate 261 (Scheme 64). 

In 2012, Teiber and Muller reported an efficient one-pot, three-component, consecutive Sonogashira-Fiesselmann cyclocondensation tandem reaction of alkyne, benzoyl chloride, and ethyl 2-mercaptoacetate to afford 2,4-disubstituted thiophenes [50]. We then developed this promising tandem reaction into the first... 

Scheme 9 Synthesis of thiophene-containing polymer P8 via three-component tandem polymerization of diyne Ic, dicarbonyl chloride 13, and ethyl 2-mercaptoacetate 14...

With the success of this three-component tandem polymerization, we further explored such polymerization by changing the third component monomer from ethyl 2-mercaptoacetate 14 to a normal thiol 16. We aimed to extend the scope of the one-pot, two-step, three-component coupling-addition tandem polymerization... 

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