Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2001(13): 2021-2027
DOI: 10.1055/s-2001-17697
DOI: 10.1055/s-2001-17697
PAPER
© Georg Thieme Verlag Stuttgart · New YorkCopper(I) Bromide-Mediated Synthesis of Novel 2-Arylthiazole-5-carboxylates from α-Diazo-β-Keto Esters and Aromatic Thioamides
Further Information
Received
22 May 2001
Publication Date:
10 August 2004 (online)
Publication History
Publication Date:
10 August 2004 (online)
Abstract
Starting from readily available α-diazo-β-keto esters 8 and aromatic primary thioamides 9 and 14, a simple synthesis of 2-aryl 4-substituted thiazole-5-carboxylate derivatives of type 10 and 16 has been accomplished. The method is based on the efficient catalysis of CuBr, which promotes the formation of the corresponding carbenoids 11 from diazo derivatives 8. These Cu-carbenoids 11 react with the thiocarbonyl group of the primary thioamides to afford presumably intermediates of the general type 12, which by subsequent cyclocondensation furnish the title thiazole derivatives.
Key words
thiazoles - primary aromatic thioamides - CuBr catalysis - α-diazo-β-keto esters - carbenoid formation
- 1 Taken in part from the Diploma Work of X.F., Universitat de Girona, 2000
- 2 Part of the planned Ph.D. Thesis of S.D., Universitat de Girona
- 3
Huisgen R.Langhals E. Tetrahedron Lett. 1989, 30: 5369 - 4a
Huisgen R.Li X. Tetrahedron Lett. 1983, 24: 4185 - 4b
Huisgen R.Fisera L.Giera H.Sustmann R. J. Am. Chem. Soc. 1995, 117: 9671 - 4c
Fisera L.Huisgen R.Kalwinsch I.Langhals E.Li X.Mloston G.Polborn K.Rapp J.Sickling W.Sustmann R. Pure Appl. Chem. 1996, 68: 789 - 5
Staudinger H.Siegwart J. Helv. Chim. Acta 1920, 3: 833 - 6
Schönberg A.König B.Singer E. Chem. Ber. 1967, 100: 767 - 7
Schönberg A.Knöfel W. Chem. Ber. 1970, 103: 938 - 8
Huisgen R. Angew. Chem. 1963, 75: 604 - 9
Kalwinsch I.Xingya L.Gottstein J.Huisgen R. J. Am. Chem. Soc. 1981, 103: 7032 - 10
Huisgen R.Mloston G.Langhals E. J. Org. Chem. 1986, 51: 4087 - 11
Kellog RM. Tetrahedron 1976, 32: 2165 - 12a
Middleton WJ. J. Org. Chem. 1969, 34: 3201 - 12b
Mloston G.Heimgartner H. Polish J. Chem. 2000, 74: 1503 - 13
Alcazar V.Tapia I.Moran JR. Tetrahedron 1990, 46: 1057 - 14
Moran JR.Tapia I.Alcazar V. Tetrahedron 1990, 46: 1783 - 15
Mloston G.Linden A.Heimgartner H. Helv. Chim. Acta 1991, 74: 1386 - 16
Mloston G.Linden A.Heimgartner H. Helv. Chim. Acta 1996, 79: 31 - 17
Buter J.Wassenaar S.Kellog RM. J. Org. Chem. 1972, 37: 4045 - 18a
Mloston G.Petit M.Linden A.Heimgartner H. Helv. Chim. Acta 1994, 77: 435 - 18b
Kägi M.Linden A.Mloston G.Heimgartner H. Helv. Chim. Acta 1996, 79: 855 - 19a
Petit M.Linden A.Mloston G.Heimgartner H. Helv. Chim. Acta 1994, 77: 1076 - 19b
Kägi M.Linden A.Mloston G.Heimgartner H. Helv. Chim. Acta 1998, 81: 285 - 20
Mloston G.Romanski J.Rusanov EB.Tshernega AN.Shermolovich JG. Russ. J. Org. Chem. 1995, 31: 1027 - 21
Kägi M.Linden A.Heimgartner H.Mloston G. Helv. Chim. Acta 1993, 76: 1715 - 22
Huisgen R.Mloston G. Heterocycles 1990, 30: 737 - 23a
Villalgordo JM.Enderli A.Linden A.Heimgartner H. Helv. Chim. Acta 1995, 78: 1983 - 23b
Kelmendi B.Mloston G.Heimgartner H. Heterocycles 2000, 52: 475 - 24
Kim G.Chu-Moyer MY.Danishefsky SJ. J. Am. Chem. Soc. 1990, 112: 2003 - 25
Kim G.Chu-Moyer MY.Danishefsky SJ.Schulte GK. J. Am. Chem. Soc. 1993, 115: 30 - 26
Fang FG.Maier ME.Danishefsky SJ. J. Org. Chem. 1990, 55: 831 - 27
Obrecht D.Villalgordo JM. Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries Tetrahedron Organic Chemistry Series, Vol. 17: Pergamon; Oxford: 1998. - 28
Obrecht D.Grieder A.Abrecht C.Villalgordo JM. Helv. Chim. Acta 1997, 80: 65 - 29
Chucholowsky A.Masquelin T.Obrecht D.Stadlwieser J.Villalgordo JM. Chimia 1996, 50: 525 - 30
Villalgordo JM. Meth. Find. Exp. Clin. Pharmacol. 1997, 19 (Suppl. A): 37 - 31
Heras M.Ventura M.Linden A.Villalgordo JM. Synthesis 1999, 1613 - 32 Diaz, S.; Villalgordo, J. M., unpublished results.
- 33
Mloston G.Gendek T.Heimgartner H. Helv. Chim. Acta 1996, 79: 1537 - 34
Honda T.Ishige H.Araki J.Akimoto S.Hirayama K.Tsubuki M. Tetrahedron 1992, 48: 79 - 35
Takano S.Tomita S.Takahashi M.Ogasawara K. Synthesis 1987, 1116 - 36
Padwa A.Kinder FR.Nadler WR.Zhi L. Heterocycles 1993, 35: 367 - 37
Capuano L.Bolz G.Burger R.Burkhardt V.Huch V. Synthesis 1994, 1219 - 38
Ledon HJ. Org. Synth. 1988, Coll. Vol. VI: 414 - 39
Oikawa Y.Yoshioka T.Sugano K.Yonemitsu O. Org. Synth. 1990, Coll. Vol. VII: 359 - 40
Fontrodona X. Diploma Work Universitat de Girona; Girona: 2000. - 41
Cox EG.Wardlaw W.Webster KC. J. Chem. Soc. 1936, 775 - 42
Johnson CK. ORTEPII 1976, Report ORNL-5138 Oak Ridge National Laboratory; Oak Ridge, Tennessee: 1976. - 43
Hargrave KD.Hess FK.Oliver JT. J. Med. Chem. 1983, 26: 1158 - 44
Patt WC.Hamilton HW.Taylor MD.Ryan MJ.Taylor DG.Connolly CJ.Doherty AM.Klutchko SR.Sircar I.Steinbaugh BA.Batley BL.Painchaud CA.Rapundalo ST.Michniewicz BM.Olson SC. J. Med. Chem. 1992, 35: 2562 - 45
Haviv F.Ratajczyk JD.DeNet RW.Kerdesky FA.Waltwers RL.Schmidt SP.Holms JH.Young PR.Carter GW. J. Med. Chem. 1988, 31: 1719 - 46
Jaen JC.Wise LD.Caprathe BW.Tecle H.Bergmeier S.Humblet CC.Heffner TG.Meltzner LT.Pugsley TA. J. Med. Chem. 1990, 33: 1453 - 48
North ACT.Phillips C.Mathews FS. Acta Crystallogr. Sect. A 1968, 24: 351 - 49
Altomare A.Cascarano G.Giacovazzo C.Guagliardi A.Burla MC.Polidori G.Camalli M. J. Appl. Crystallogr. 1994, 27: 435 - 50
teXsan, Single Crystal Structure Analysis Software, Version 1.10
Molecular Structure Corporation;
The Woodlands, TX:
1999.
References
Crystallographic data (excluding structure factors)for the structure of 16b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-158835. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. (fax: +44(1223)336033; email: deposit@ccdc.cam.ac.uk).