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Synlett 2010(3): 501-502
DOI: 10.1055/s-0029-1219338
DOI: 10.1055/s-0029-1219338
SPOTLIGHT
© Georg Thieme Verlag
Stuttgart ˙ New York
Ethyl 2-Cyano-3,3-bis(methylthio)acrylate
Dedicated to my father late B. M. Kalyankar and dedicated to my supervisor Dr. S. V. Bhosale (Reader) on the occasion of his 37th birthday.
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
25. Januar 2010 (online)
Biographical Sketches
Introduction
Ethyl 2-cyano-3,3-bis(methylthio)acrylate (Figure [¹] ) was prepared by the reaction of ethyl cyanoacetate, carbon disulfide and dimethyl sufate in the presence of a base. [¹] Gommper and co-workers studied this reaction thoroughly. The electron-attracting groups on C2 makes it a very useful reagent for the preparation of heterocyclic compounds. [²] Moreover, Ethyl 2-cyano-3,3-bis(methylthio)acrylate can also be prepared efficiently using sodium ethoxide as a base. [³] In the literature numerous reports appeared highlighting its chemistry and use.
Abstracts
(A) Tominaga et al. reported the synthesis of 2H-pyran-2-one starting from acetophenones and ethyl 2-cyano-3,3-bis(methylthio)acrylate in the presence of KOH in DMF. [4] | |
(B) The 2H-pyran-2-one derivatives have been prepared by reacting an aryl methyl ketone and 1,2-diarylethanone with methyl 2-cyano-3,3-bis(methylthio)acrylate in the presence of KOH in DMF. [5] | |
(C) Baheti et al. described the synthesis of 4H-pyrimido[2,1-b]benzothiazole-8-substituted 2-thiomethyl-3-cyano-4-ones by the reaction of 2-amino-6-substituted benzothiazole with ethyl 2-cyano-3,3-bis(methylthio)acrylate in the presence of anhydrous potassium carbonate in DMF. [6] The synthesized compounds were further investigated for analgesic and CNS-depressant activity. | |
(D) Recently, the group of V. J. Ram described the synthesis of 4-methylsulfanyl-2-oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitriles by the reaction between 1-tetralone and methyl 2-cyano-3,3-dimethylthioacrylate in the presence of KOH/DMSO in catalytic amounts. [7] | |
(E) The condensation reaction between ethyl 2-cyano-3,3-bis(methylthio)acrylate and alkyl 2-mercaptoacetate leading to highly functionalized thiophenes was reported by V. J. Ram and co-workers. [8] | |
(F) Suitably functionalized pyrimidine derivatives were synthesized by condensation of ethyl 2-cyano-3,3-dimethylthioacrylate with amidine. [9] Kohara and co-workers also synthesized pyrimidine derivatives starting from ketene dithioacetal and amides in the presence of sodium hydride in DMA. [9] | |
(G) Mukharjee et al. reported the synthesis of pyridopyrimidine starting from cyanoketene dithioacetal and 2-aminopyridine in the presence of triethylamine in benzene. [¹0] | |
(H) The synthesis of triazepines was described by Omran et al. by condensation of N,N′-diphenylpiperidine-1-carbohydrazonamide with ethyl 2-cyano-3,3-dimethylthioacrylate in the presence of t-BuOH and TEA. [¹¹] | |
(I) Yang and co-workers describe the synthesis of 3-aryl-5-cyano-6-methylthio pyrimidine-2,4-diones from ethyl 2-cyano-3,3-dimethylthioacrylate with arylureas in toluene and DMA under mild condition. [¹²] | |
(J) Novel ketene N,S-acetals were prepared by the reaction of ethyl 2-cyano-3,3-bis(methylthio)acrylate with low nucleophilic aromatic amines using sodium hydride in toluene. [¹³] | |
(K) Metwally and co-workers described the reaction of ethyl 2-cyano-3,3-bis(methylthio)acrylate with aminoazoles (5-aminotetrazole monohydrate and 2-aminothiazole) in the presence or absence of triethylamine leading to the corresponding pyrimidines. [¹4] |
- 1
Gompper R.Topfl W. Chem. Ber. 1962, 95: 2861 -
2a
Chauhan SMS.Junjappa H. Tetrahedron 1976, 32: 1779 -
2b
Chauhan SMS.Junjappa H. Tetrahedron 1976, 32: 1911 -
2c
Potts KT.Cipullo MJ.Ralli P.Theodoridis G. J. Am. Chem. Soc. 1981, 103: 3584 -
2d
Kumar A.Mhatra S.Ila H.Junjappa H. J. Chem. Soc. Chem. Commun. 1976, 592 - 3
Kumar A.Malhotra S.Vats A. .Singh SK.Sharma SK.Prasad AK.Errington W.Olsen CE.Jain SC.Parmar VS. Indian J. Chem. 2002, 41B: 360 - 4
Tominaga Y.Ushirogochi A.Matsuda Y.Kobayashi G. Chem. Pharm. Bull. 1984, 32: 3384 -
5a
Ram VJ.Verma M. Indian J. Chem. 1990, 29B: 624 -
5b
Pratap R.Kumar B.Ram VJ. Tetrahedron 2007, 63: 10300 -
5c
Singh FV.Vatsyayan R.Roy U.Goel A. Bioorg. Med. Chem. Lett. 2006, 16: 2734 - 6
Baheti KG.Kuberkar SV. Indian J. Heterocycl. Chem. 2003, 12: 343 -
7a
Pratap R.Ram VJ. Tetrahedron Lett. 2007, 48: 4715 -
7b
Pratap R.Ram VJ. J. Org. Chem. 2007, 72: 7402 - 8
Ram VJ.Goel A.Shukla PK.Kapil A. Bioorg. Med. Chem. Lett. 1997, 7: 3101 -
9a
Agarwal N.Raghuwanshi SK.Upadhyay DN.Shukla PK.Ram VJ. Bioorg. Med. Chem. Lett. 2000, 10: 703 -
9b
Kohra S.Tominaga Y.Hosomi AJ. Heterocycl. Chem. 1988, 25: 959 - 10
Mukherjee-Singh O.Farooque MA. Indian J. Chem. 2004, 43B: 1561 - 11
Omran OA.Amer AA.Khodairy A. Synth. Commun. 2006, 36: 3647 - 12
Liu H.Yang G.Chen K.Yang H. Synth. Commun. 1999, 29: 3143 - 13
Liu H.Lu R.Yang H. Synth. Commun. 1998, 28: 3965 - 14
Metwally MA.Desoky EI.Fawzy R.Etman HA. Chem. Heterocycl. Compd. 2007, 43: 382
References
- 1
Gompper R.Topfl W. Chem. Ber. 1962, 95: 2861 -
2a
Chauhan SMS.Junjappa H. Tetrahedron 1976, 32: 1779 -
2b
Chauhan SMS.Junjappa H. Tetrahedron 1976, 32: 1911 -
2c
Potts KT.Cipullo MJ.Ralli P.Theodoridis G. J. Am. Chem. Soc. 1981, 103: 3584 -
2d
Kumar A.Mhatra S.Ila H.Junjappa H. J. Chem. Soc. Chem. Commun. 1976, 592 - 3
Kumar A.Malhotra S.Vats A. .Singh SK.Sharma SK.Prasad AK.Errington W.Olsen CE.Jain SC.Parmar VS. Indian J. Chem. 2002, 41B: 360 - 4
Tominaga Y.Ushirogochi A.Matsuda Y.Kobayashi G. Chem. Pharm. Bull. 1984, 32: 3384 -
5a
Ram VJ.Verma M. Indian J. Chem. 1990, 29B: 624 -
5b
Pratap R.Kumar B.Ram VJ. Tetrahedron 2007, 63: 10300 -
5c
Singh FV.Vatsyayan R.Roy U.Goel A. Bioorg. Med. Chem. Lett. 2006, 16: 2734 - 6
Baheti KG.Kuberkar SV. Indian J. Heterocycl. Chem. 2003, 12: 343 -
7a
Pratap R.Ram VJ. Tetrahedron Lett. 2007, 48: 4715 -
7b
Pratap R.Ram VJ. J. Org. Chem. 2007, 72: 7402 - 8
Ram VJ.Goel A.Shukla PK.Kapil A. Bioorg. Med. Chem. Lett. 1997, 7: 3101 -
9a
Agarwal N.Raghuwanshi SK.Upadhyay DN.Shukla PK.Ram VJ. Bioorg. Med. Chem. Lett. 2000, 10: 703 -
9b
Kohra S.Tominaga Y.Hosomi AJ. Heterocycl. Chem. 1988, 25: 959 - 10
Mukherjee-Singh O.Farooque MA. Indian J. Chem. 2004, 43B: 1561 - 11
Omran OA.Amer AA.Khodairy A. Synth. Commun. 2006, 36: 3647 - 12
Liu H.Yang G.Chen K.Yang H. Synth. Commun. 1999, 29: 3143 - 13
Liu H.Lu R.Yang H. Synth. Commun. 1998, 28: 3965 - 14
Metwally MA.Desoky EI.Fawzy R.Etman HA. Chem. Heterocycl. Compd. 2007, 43: 382