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Synthesis 2004(5): 675-678
DOI: 10.1055/s-2004-815972
DOI: 10.1055/s-2004-815972
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Mild and Efficient Procedure for the Synthesis of 1-(Alkyldithiocarbonyl)-imidazoles
Weitere Informationen
Received
28 November 2003
Publikationsdatum:
12. Februar 2004 (online)
Publikationsverlauf
Publikationsdatum:
12. Februar 2004 (online)
Abstract
1-(Alkyldithiocarbonyl)-imidazoles, 1-(methyldithio- carbonyl)-1,2,4-triazole and 1-(methyldithiocarbonyl)-benzotriazole were prepared in good to excellent yields from the reaction of imidazol, 1,2,4-1H-triazole and 1H-benzotriazole with carbon disulfide and corresponding alkylating agents in the presence of anhydrous potassium phosphate in acetone at room temperature within 2 hours.
Key words
1-(alkyldithiocarbonyl)-imidazole - thiocarbonyl transfer reagent - synthesis - anhydrous potassium phosphate - imidazole
- 1
Thorn GD.Ludwig RA. The Dithiocarbamates and Related Compounds Elsevier; Amsterdam: 1962. - 2
Safak C.Erdogan H.Yesilada A.Erol K.Cimgi I. Arzneim. Forsch. 1992, 42: 123 -
3a
Aboul-Fadl T.El-Shorbagi A. Eur. J. Med. Chem. 1996, 31: 165 -
3b
Cascio G.Lorenzi L.Caglio D.Manghisi E.Arcamone F.Guanti G.Satta G.Morandotti G.Sperning R. Farmaco. 1996, 51: 189 -
3c
Imamura H.Ohtake N.Jona H.Shimizu A.Moriya M.Sato H.Sugimoto Y.Ikeura C.Kiyonaga H.Nakano M.Hagano R.Abe S.Yamada K.Hashizume T.Morishima H. Bioorg. Med. Chem. Lett. 2001, 9: 1571 -
3d
Nagano R.Shibata K.Naito T.Fuse A.Asano K.Hashizume T.Nakagawa S. Antimicrob. Agents Chemother. 1997, 41: 2278 -
4a
Gerhauser C.You M.Liu J.Moriarty RT.Hawthorne M.Mehta RG.Moon RC.Pezzuto JM. Cancer Research 1997, 57: 272 -
4b
Scozzafava A.Mastorlorenzo A.Supuran CT. Bioorg. Med. Chem. Lett. 2000, 10: 1887 -
4c
Ge ZM.Li RT.Cheng TM.Cui JR. Arch. Pharm. Pharm. Med. Chem. 2001, 334: 173 - 5
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley-Interscience; New York: 1999. p.484-486 - 6
Kanie K.Mizuno K.Kuroboshi M.Hiyama T. Bull. Chem. Soc. Jpn. 1998, 71: 1973 -
7a
Sugimoto H.Makino I.Hirai K. J. Org. Chem. 1988, 53: 2263 -
7b
Takikawa Y.Inoue N.Sato R.Takizawa S. Chem. Lett. 1982, 641 -
8a
Alajarin A.Vidal A.Ortin MM. Tetrahedron Lett. 2003, 44: 3027 -
8b
Quiclet-Sire B.Quintero L.Sanchez-Jimenez G.Zard SZ. Synlett 2003, 75 -
8c
Quiclet-Sire B.Sanchez-Jimenez G.Zard SZ. Chem. Commun. 2003, 1408 -
8d
Yadav LDS.Singh A. Tetrahedron Lett. 2003, 44: 5637 -
8e
Katritzky AR.Bayyuk S. Heterocycles 1985, 23: 3099 -
9a
Gomez L.Gellibert F.Wagner A.Mioskowski C. J. Comb. Chem. 2002, 2: 75 -
9b
Whitehead DM.Jackson T.Mckeown SC.Wilson K.Routledge A. J. Comb. Chem. 2002, 2: 255 -
9c
Perez R.Reyes O.Suarez M.Garay HE.Cruz LJ.Rodriguez H.Moleo-Vilchez MD.Ochoa C. Tetrahedron Lett. 2000, 41: 613 - 10
Burke TR.Bajwa BS.Jacobson AE.Rice KC.Streaty RA.Klee WA. J. Med. Chem. 1984, 27: 1570 - 11
Walter W.Bode K.-D. Angew. Chem., Int. Ed. Engl. 1967, 6: 281 -
12a
Lieber E.Orlowski RO. J. Org. Chem. 1957, 22: 88 -
12b
Lee AWM.Chan WH.Wong HC.Wong MS. Synth. Commun. 1989, 19: 547 -
12c
Degani I.Fochi R. Synthesis 1978, 365 -
13a
Salvatore RN.Sahab S.Jung KW. Tetrahedron Lett. 2001, 42: 2055 -
13b
Nagle AS.Salvatore RN.Cross RM.Kapxhiu EA.Sahab S.Yoon CH.Jung KW. Tetrahedron Lett. 2003, 44: 5695 - 14
Pujol MD.Guillaumet G. Synth. Commun. 1992, 22: 1231 -
15a
Li RT.Ding PY.Han M.Cai MS. Synth. Commun. 1998, 28: 295 -
15b
Li RT.Cai MS. Synth. Commun. 1999, 29: 65 -
15c
Ge ZM.Li RT.Cheng TM. Synth. Commun. 1999, 29: 3191 -
15d
Li RT.Ge ZM.Cheng TM.Cai MS. Chem. J. Chin. Univ. 1999, 20: 1897 -
15e
Guo BG.Ge ZM.Cheng TM.Li RT. Synth. Commun. 2001, 31: 3021 -
15f
Cui JL.Ge ZM.Cheng TM.Li RT. Synth. Commun. 2003, 33: 1969 - 16
Mohanta PK.Dhar S.Samal SK.Ila H.Junjappa H. Tetrahedron 2000, 56: 629 - 17
Howes PD.Pianka M. J. Chem. Soc., Perkin Trans. 1 1980, 762 - 18
Shi YP.Sun WY.Hu JQ. Synlett 1997, 1279 -
19a
Katritzky AR.Lan X.Yang JZ.Denisko O. Chem. Rev. 1998, 409 -
19b
Katritzky AR.Toader D. Synlett 2001, 458 -
19c
Katritzky AR.Pastor A.Voronkov M.Tymoshenko D. J. Comb. Chem. 2001, 3: 167 -
19d
Katritzky AR.Rogovoy BV. Chem.-Eur. J. 2003, 9: 4586