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Synthesis 2002(12): 1646-1648
DOI: 10.1055/s-2002-33636
DOI: 10.1055/s-2002-33636
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of N-Substituted Thiazolidines and Dihydrobenzothiazoles
Further Information
Received
15 January 2002
Publication Date:
05 September 2002 (online)
Publication History
Publication Date:
05 September 2002 (online)
Abstract
Ethyl (4R)-3-(1H-1,2,3-benzotriazol-1-ylmethyl)-1,3-thiazolane-4-carboxylate (6) and 1-[1,3-benzothiazol-3(2H)-ylmethyl]-1H-1,2,3-benzotriazole (8) were readily prepared by reactions of l-cysteine ethyl ester hydrochloride and 1-aminothiophenol with benzotriazole and formaldehyde, respectively. Chiral thiazolidine esters 7a-c were obtained by reactions of intermediate 6 with organozinc derivatives. Nucleophilic substitutions of 8 with Grignard reagents gave N-substituted dihydrobenzothiazoles 9a-c.
Key words
benzotriazole - thiazolidine - dihydrobenzothiazole - cyclocondensation - organozinc reagent
-
1a
Panizzi L. Gazz. Chim. Ital. 1948, 78: 207 ; Chem. Abstr. 1948, 42, 7294 -
1b
Wasserman HH.Precopio FM.Liu T.-C. J. Am. Chem. Soc. 1952, 74: 4093 -
1c
Cooper RDG.Jose FL. J. Am. Chem. Soc. 1974, 94: 1021 - 2
Fairweather R.Jones JH. J. Chem. Soc., Perkin Trans 1 1972, 2475 - 3
Pellegrini N.Refouvelet B.Crini G.Blacque O.Kubicki MM.Robert J.-F. Chem. Pharm. Bull. 1999, 47: 950 - 4
Zeidler J.Zimmermann W. Chem. Phys. Lipids 1995, 75: 183 - 5
Garg A.Tandon JP. Bull. Chem. Soc. Jpn. 1989, 62: 3760 -
6a
Calo V.Nacci A.Lopez L.Mannarini N. Tetrahedron Lett. 2000, 41: 8973 -
6b
Calo V.Sole RD.Nacci A.Schingaro E.Scordari F. Eur. J. Org. Chem. 2000, 869 - 7
Phillips RC. inventors; European Patent 133481. ; Chem. Abstr. 1985, 102, 144661 - 8
Kaneko Y. inventors; Japanese Patent 63149644. ; Chem. Abstr. 1989, 111, 47985 - 9
Balny C.Guglielmetti R.Mosse M.Metzger J. Photochem. Photobiol. 1972, 16: 69 ; Chem. Abstr. 1972, 77, 113289 - 10
Davin-Pretelli E.Guiliano M.Mille G.Chouteau J.Guglielmetti R.Gelebart C. Helv. Chim. Acta 1977, 60: 215 ; and references cited therein - 11
Refouvelet B.Harraga S.Nicod L.Robert J.-F.Seilles E.Couquelet J.Tronche P. Chem. Pharm. Bull. 1994, 42: 1076 - 12
Trentmann W.Mehler T.Martens J. Tetrahedron: Asymmetry 1997, 8: 2033 -
13a
Ratner S.Clarke HT. J. Am. Chem. Soc. 1937, 59: 200 -
13b
Lewis NJ.Inloes RL.Hes J. J. Med. Chem. 1978, 21: 1070 - 14
Gonzalez A.Lavilla R. Tetrahedron 1995, 51: 3015 - 15
Hamri A.Pera M.-H.Valenti R.Boucherle A. Arch. Pharm. (Weinheim, Ger.) 1985, 318: 707 - 16
Zeidler JM.Emling F.Zimmermann W.Roth HJ. Arch. Pharm. (Weinheim, Ger.) 1991, 324: 687 - 17
Magni A.Signorelli G.Bocchiola G. Drug Res. 1994, 44: 1402 - 18
Inamori Y.Muro C.Yamanaka H.Osaka K.Hachiken H. Biosci. Biotechnol. Biochem. 1994, 58: 1150 - 19
Hori M.Kataoka T.Shimizu H.Imai Y. Chem. Pharm. Bull. 1979, 27: 1973 - 20
Muren JF.Weissman A. J. Med. Chem. 1971, 14: 49 - 21
Somogyi L. Z. Naturforsch. 1982, 37B: 838 ; Chem. Abstr. 1982, 97, 109655 - 22
Baker K.Fierz-David HE. Helv. Chim. Acta 1950, 33: 2011 - 23
Mruthyunjayaswamy BHM.Shanthaveerappa BK. Indian J. Chem., Sect. B 2000, 39: 433 - 24
Larive H.Chambonnet AJ.Metzger J. Bull. Soc. Chim. Fr. 1963, 1675 - 25
Katritzky AR.Lan X.Yang JZ.Denisko OV. Chem. Rev. 1998, 98: 409 - 26
Katritzky AR.Rachwal S.Hitchings GJ. Tetrahedron 1991, 47: 2683 -
27a
Katritzky AR.Urogdi L.Mayence A. Synthesis 1989, 323 -
27b
Katritzky AR.Odens HH.Voronkov MV. J. Org. Chem. 2000, 65: 1886 -
27c
Katritzky AR.Mehta S.He H.-Y.Cui X. J. Org. Chem. 2000, 65: 4364 - 28
Akiba K.-Y.Ohara Y.Inamoto N. Bull. Chem. Soc. Jpn. 1982, 55: 2976