Heteroannulation through copper catalysis: A novel cyclization leading to a highly regio- and stereoselective synthesis of 2-substituted benzothiazolines

Organic Letters

Volumn 2, Issue 3, 2000, Pages 235-238

  Nandi, Bidisha ^a   Kundu, Nitya G ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000526641     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990165g     Document Type: Article

References (48)

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26. For references on naturally occurring and biologically active benzofurans, phthalides, quinolines, isoindolinones, and isobenzofurans, see references cited in 4a-e.
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28. Chowdhury, C.; Kundu, N. G. Chem. Commun 1996, 1067. Chowdhury, C.; Chaudhuri, G.; Guha, S.; Mukherjee, A. K.; Kundu, N. G. J. Org. Chem. 1998, 63, 1863.
29. Chaudhuri, G.; Chowdhury, C.; Kundu, N. G. Synlett 1998. 11, 1273.
30. When the tosylate of 8 was used under similar conditions or with excess CuI (40 mol %), neither disubstituted alkynes 19-28 nor cyclic products 29-38 could be obtained.
31. The use of less CuI led to lower yields - for example with 19, use of 6 mol % of CuI gave 10% yield, similarly 20 mol % gave 30% yield, 30 mol % gave 45% yield, and 40 mol % gave 67% yield of 29. Higher percentages of CuI led to a decline in yield. Also, the use of KOH in the cyclization step did not give any cyclic product, with the detosylated amines being recovered.
32. 3, TMS, 25 °C): δ 21.516, 68.958, 120.87, 122.620, 125.321, 125.638, 126.853, 126.911, 127.367, 128.047, 128.374, 129.376, 130.650, 132.572, 134.539, 136.897, 144.243.
33. 1H NMR spectra.
34. Corey, E. J.; Boger, D. L. Tetrahedron Lett. 1978, 5.
35. To be reported in detail elsewhere.
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38. For general references, see: Metzer, J. V. Thiazoles and their Benzo derivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 6, p 235.
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41. (c) As anticonvulsant, vasodilators, and blood platelet aggregation inhibitors: Santen Pharmaceutical Co. Ltd. Jpn. Kokai, Tokyo Koho, JP 5967, 27 [8467, 276]; Chem. Abstr. 1985, 102, 6464a. Ucar, H.; Vanderpoorten, K.; Cacciaguerra, S.; Spampinato, S.; Stables, J. P.; Depovere, P.; Isa, M.; Masereel, B.; Delarge, J.; Poupaert, J. H. J. Med. Chem. 1998, 41, 1138.
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47. 4). After removal of solvent, the residue was chromatographed on silica gel (60-120 mesh), with the eluant being 5% ethyl acetate in light petroleum (60-80 °C), to yield the disubstituted alkynes 19-28.
48. 4) and the solvent was removed. The residue was purified by column chromatography on silica gel (60-120 mesh), with the eluant being 5% ethyl acetate in light petroleum (60-80 °C). Compound 29 was crystallized from chloroform-petroleum ether (60-80 °C), mp 154 °C.