Synthèses D'indoles Et d'Indolizines Marqués Spécifiquement par 13C dans le Cycle Pentagonal

作者: M. F. Lautie , M. Corval

DOI: 10.1002/JLCR.2580190903

关键词:

摘要: The syntheses of 2-13C and 3-13C indoles indolizines 1-13C indolizine are described. They obtained from bromoacetaldehyde on (2-pyridyl) ethylacetate for indolizine, through cyclisations suitably labelled intermediates:o-formotoluidide indole, o,β-dinitrostyrene 3-(2-pyridyl)-1 propanol indolizines. Every position is more than 90% 13C- labelled.

参考文章(14)
Shigehiko Sugasawa, Hisayuki Matsuo, Synthesis of α, β-Unsaturated Esters by Application of Wittig Reaction Chemical & Pharmaceutical Bulletin. ,vol. 8, pp. 819- 826 ,(1960) , 10.1248/CPB.8.819
John L. Roberts, C. Dale Poulter, 2′,3′,5′-Tri-O-benzoyl[4-13C]uridine. An efficient, regiospecific synthesis of the pyrimidine ring Journal of Organic Chemistry. ,vol. 43, pp. 1547- 1550 ,(1978) , 10.1021/JO00402A014
John Harley-Mason, 42. Melanin and its precursors. Part VI. Further syntheses of 5 : 6-dihydroxyindole and its derivatives Journal of the Chemical Society (Resumed). pp. 200- 203 ,(1953) , 10.1039/JR9530000200
W. Davey, J. R. Gwilt, 47. The preparation of the mononitrobenzaldehydes Journal of The Chemical Society (resumed). pp. 204- 208 ,(1950) , 10.1039/JR9500000204
D. R. Bragg, D. G. Wibberley, 609. Indolizines. Part II. Preparation from ethyl 2-pyridylacetate and related compounds Journal of the Chemical Society (Resumed). pp. 3277- 3281 ,(1963) , 10.1039/JR9630003277
Lester Friedman, Anthony T. Jurewicz, Procedure for the preparation of low-boiling alcohols and amines via lithium aluminum hydride and deuteride reduction Journal of Organic Chemistry. ,vol. 33, pp. 1254- 1255 ,(1968) , 10.1021/JO01267A075
David M. Grant, Ronald J. Pugmire, Morris J. Robins, Ronald K. Robins, Carbon-13 magnetic resonance. XX. 4-Azaindene (pyrrocoline) and related bridgehead nitrogen heterocycles Journal of the American Chemical Society. ,vol. 93, pp. 1887- 1893 ,(1971) , 10.1021/JA00737A009
E. J. Merril, G. G. Vernice, Synthesis of picolinic-(carboxyl-14C) acid and 2-{(methylsulfinyl) acetyl - (carbonyl -14C)} pyridine Journal of Labelled Compounds and Radiopharmaceuticals. ,vol. 8, pp. 589- 593 ,(1972) , 10.1002/JLCR.2590080406
M. Scholtz, Die Einwirkung von Essigsäureanhydrid auf α-Picolin Berichte der deutschen chemischen Gesellschaft. ,vol. 45, pp. 734- 746 ,(1912) , 10.1002/CBER.191204501108
V. Boekelheide, R. J. Windgassen, Syntheses of Pyrrocolines Unsubstituted in the Five-membered Ring1 Journal of the American Chemical Society. ,vol. 81, pp. 1456- 1459 ,(1959) , 10.1021/JA01515A044