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Please login to access the full content or check if you have access via11.17.1.5.2.5 Method 5: From (Ethoxycarbonylmethyl)imidodithiocarbonate or Ethyl {[1-(Methylsulfanyl)alkylidene]amino}acetates
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Kikelj, D.; Urleb, U., Science of Synthesis, (2002) 11, 690.
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]
Meeeee 88 Meeeeeeee ee Meeee Meeeeeee-8-eeeeeeeeeeee eeee ee (Meeeeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee ee Meeee {[8-(Meeeeeeeeeeeee)eeeeeeeeee]eeeee}eeeeeee[888–888]
M8 | M8 | M—M Meeeeee | Meee | Mee- eeee | Meee (°M) | Meee (e) | Meeee (%) | ee (°M) | Mee |
---|---|---|---|---|---|---|---|---|---|
MMe | MMe | MM8 | e-MeMM | MMM | −88 | 8.8 | 88e | 88–88 | [888] |
MMe | MMM8Me | MM8 | e-MeMM | MMM | 8 ee ee | 8 | 88e | 88 | [888] |
MMe | MMMe | MeMMM | e-MeMM | MMM | −88 ee ee | 8 | 88 | eee | [888] |
MMe | MMMe | MeMMM | e-MeMM | MMM | −88 ee ee | 8 | 88 | 88–88 | [888] |
MMe | Me | MeMM8Me | e-MeMM | MMM | −88 ee ee | 8 | 88e | eee | [888] |
MMe | Me | MeMM8Me | e-MeMM | MMM | −88 ee ee | 8 | 88e | 88–88 | [888] |
M | Me | MeMMMMe | MMM | MMM | eeeeee | 8.8 | 88 | eee | [888] |
Me | 8-eeeee | MMM | MMM | eeeeee | 8.8 | 88 | 88–88 | [888] | |
Me | Me | MeMMMMe | MMM | MMM | eeeeee | 8.8 | 88 | 888–888.8 | [888] |
e Meeee ee eeee eeeeeeeeee eeee MeMe.
e Meeee ee eeee eeeeeeeeee eeee MeMM8M.
e M eeeeeeeeeee eeeeee ee eee eeeeeeeeeeeee 8-eeeeeeeeee eeee ee eeeeee ee eeeeeeeeee ee eee eeeeeee eeeeee eeeeeee eeeeee. Meeee eeeee ee. 88%.
Meeeeeeeeeee Meeeeeeeee
Meeee 8,8-Meeeeeeeeeeeeeee-8-eeeeeeeeeee (888, M8 = M8 = Me); Meeeeee Meeeeeeee:[888]
M eeeeeee ee eeeee [[(eeeeeeeeeeeeee)(eeeeee)eeeeeeeee]eeeee]eeeeeee (888 ee, 8.8 eeee), M-eeeee eeeeeeeeeeee (888 ee, 8.8 eeee), MMM (888.8 ee, 8.8 eeee), eee MMM (8 eM) eee eeeeee ee eeeeee eeeee eeeee eee 8.8 e. Mee eeeeeee eee eeeeee eeee M8M eee eeeeeeeee eeee Me8M. Mee Me8M eeeeeee eee eeeee (Me8MM8), eee eeeee ee eeee e eeeeee eee, eeeee eee eeeeeeee ee eeeeeeeeeee MMM (MeMMe/eeeeee, 8:8) ee eeee eee eeeeeee; eeeee: 888 ee (88%); ee 888–888.8°M.
Meeee 8-(Meeeeeeeee/eeeeeeeee)-8-(eeeeeeeeeeeeee)eeeeeeee-8-eeeeeeeeeeee 888 (M8 = MMe; M8 = eeeeeeeeee ee eeeeeeeee); Meeeeee Meeeeeeee:[888]
Me e eeeeeee eeee ee e-MeMM (8.888 e, 8 eeee) ee eee MMM (88 eM) eee eeeee eeeeeeee ee −88°M eeeee M8 e eeee ee eeeeeeee (eeeeeeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeeeeee (8 e, 8 eeee) ee eee MMM (8 eM). Meeee 8.8 e ee −88°M, e eeee ee ee eeeeeeeeeeeeee (8 eeee) ee eee MMM (8 eM) eee eeeeee eeeee. Meeee 88 eee ee −88°M, eee eeeeeee eee eeeeeee ee eeeee ee ee eee 8 e, eee eee eeee eeeeeeee eeee M8M, eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8, 88 e) eee eeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeee eeeeeee eee eeeeeeee eeeeee ee eeeeeeeeeeeeeee ee ee eeeee eeeeeeeeeeeeee ee eeeeee eee.
References
[497] | Meeeeee-Meeeee, M.; Máeeee, M.; Meeee, M.; Meeee, M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[498] | Möeeeee, M.; Meeee, M.; Meeeeeee, M., M. Meee., (8888) 88, 888. |
[499] | Meeeeee-Meeeee, M.; Mee, M.; Meeee, M.; Meeeeee, M. M., Meeeeeeeeeee, (8888) 88, 8888. |
[500] | Meeeeee, M.; Meeeeee-Meeeee, M.; Meeeeeee, M.; Meeeeee, M. M., Meee. Mee. Meee. Meee., (8888) 88, 888. |
[501] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meee, M., Meeeeeeee, (8888), 8888. |
[502] | Meeeeeee, M., Meeeeeeeee Meeeee Meeeeee Meeee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.