Synthesis, Inhaltsverzeichnis Synthesis 2014; 46(01): 96-100DOI: 10.1055/s-0033-1338577 paper © Georg Thieme Verlag Stuttgart · New YorkA Convenient Preparation of Thieno[3,2-c]pyrazole[1] John Airey , Matthieu Barrague , Michael L. Edwards , Michael Ferro , Dirk Friedrich , Timothy A. Gillespy , John Jurcak , Kwon Musick , Philip M. Weintraub* Artikel empfehlen Abstract Alle Artikel dieser Rubrik Abstract A practical synthesis of multigram quantities of 1H-thieno[3,2-c]pyrazole is presented in which the Jacobson reaction serves as the key step. Key words Key wordsaminations - cyclizations - polycycles - heterocycles Volltext Referenzen References 1 Heterocycles, part 14. For part 13, see: Weintraub PM. J. Heterocycl. Chem. 1993; 30: 1635 2 Current address: Retired. 3 Current address: Chemical Research, Sanofi US, 153 2nd Ave, Waltham, MA 02451, USA. 4 Current address: 33 Casale Drive South, Warren, NJ 07059, USA. 5a Görtz R, Appelboom T. Int. J. 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Am. Chem. Soc. 1959; 81: 610 For similar alane reductions, see also: 16b Wigfield DC, Taymaz K. Tetrahedron Lett. 1973; 4841 16c Tucker H. J. Med. Chem. 1980; 23: 1122 17 Moody CJ, Shah P. J. Chem. Soc., Perkin Trans. 1 1989; 2463 18 Fuller LS, Iddon B, Smith KA. J. Chem. Soc., Perkin Trans. 1 1997; 3465 19 An aliquot was removed and worked up by filtration, concentration of the filtrate, and chromatography of the residue. Combination and concentration of amide-containing fractions gave N-(2-methyl-3-thienyl)acetamide as a light-beige solid. 1H NMR: δ = 2.18 (s, 3 H), 2.31 (s, 3 H), 7.01 (d, 1 H), 7.27 (d, 1 H). 13C NMR: δ = 12.25, 23.73, 120.69, 124.34, 126.10, 131.49, 167.84. Anal. Calcd for C7H9NOS: C, 54.17; H, 5.84; N, 8.78; S, 20.66. Found: C, 53.92; H, 5.86; N, 8.78; S, 20.51. 20 Although the Jacobson reaction has been shown to yield a mixture of N 1-acetyl and N 2-acetyl tautomers, we never obtained any of the N 2-acetyl material. 21 Gronowitz S, Moses P, Hörnfeld A.-B, Hakansson R. Ark. Kemi 1961; 17: 165
