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2O (2 mL) was irradiated at 150 °C in a sealed glass tube (150 W) for 10 min and evaporated in vacuo to give 2·HCl (151 mg, >98%). Comparable conductive heating procedures carried out at 150 °C in a sealed tube for 12 min, or at reflux for 30 min, gave thiazole 2·HCl (90% or 85%, respectively, by HPLC). For related hydrolysis experiments using conductive heating, see: (a) Houssin, R.; Pommery, J.; Salauen, M.-C.; Deweer, S.; Goossens, J.-F.; Chavatte, P.; Henichart, J.-P. J. Med. Chem. 2002, 45, 533.
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2 eluting with light petroleum-EtOAc (9:1). For related Fischer indole syntheses, see: (a) An, J.; Bagnell, L.; Cablewski, T.; Strauss, C. R.; Trainor, R. W. J. Org. Chem. 1997, 62, 2505.
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52
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33645175353
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note
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The glass tube was filled with standard quartz sand, 40-100 mesh, suitable for use in chromatography. When aminodienonè 5 was irradiated in toluene (without acetic acid) in the presence and absence of sand in a sealed tube, no appreciable difference was observed (13% versus 5% conversion, respectively), indicating that the sand has a negligible (if any) effect on the cyclodehydration.
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With simultaneous cooling, IR temperature measurement may not record the accurate bulk temperature of the reaction mixture; see: Leadbeater, N. E.; Pillsbury, S. J.; Shanahan, E.; Williams, V. A. Tetrahedron 2005, 61, 3565.
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Leadbeater, N.E.1
Pillsbury, S.J.2
Shanahan, E.3
Williams, V.A.4
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Houssin, R.; Pommery, J.; Salaün, M.-C.; Deweer, S.; Goossens, J.-F.; Chavatte, P.; Hénichart, J.-P. J. Med. Chem. 2002, 45, 533.
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Houssin, R.1
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Deweer, S.4
Goossens, J.-F.5
Chavatte, P.6
Hénichart, J.-P.7
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