Indanones and indenols from 2-alkylcinnamaldehydes via the intramolecular Friedel-Crafts reaction of geminal diacetates.
作者： Gary B. Womack , John G. Angeles , Vincent E. Fanelli , Brinda Indradas , Roger L. Snowden
DOI: 10.1021/JO900910B
关键词:
摘要: When treated with Ac2O at rt in the presence of 4−6 mol % FeCl3, 2-alkylcinnamaldehydes are converted to 2-alkyl-1H-inden-1-yl acetates through intermediacy gem-diacetates. Methanolysis indenyl yields corresponding indenols. Saponification 2-alkylindanones, providing, effect, an intramolecular acylation employing catalytic levels acid.
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sci-hub.se 参考文章(49)
MASAMICHI FUKUOKA, KUNITOSHI YOSHIHIRA, SHINSAKU NATORI, KUNIHIDE MIHASHI, MASATOSHI NISHI, Carbon-13 nuclear magnetic resonance spectra of pterosin-sesquiterpenes and related indan-1-one derivatives. CHEMICAL & PHARMACEUTICAL BULLETIN. ,vol. 31, pp. 3113- 3128 ,(1983) , 10.1248/CPB.31.3113
Pierre-Yves Blanc, Etude de quelques énolacylates diéniques et leur utilisation dans une méthode générale de synthèse d'anhydrides phtaliques substitués Helvetica Chimica Acta. ,vol. 44, pp. 1- 12 ,(1961) , 10.1002/HLCA.19610440102
Vladimir Gevorgyan, Long Guo Quan, Yoshinori Yamamoto, Synthesis of indenols and indanones via catalytic cyclic vinylpalladation of aromatic aldehydes Tetrahedron Letters. ,vol. 40, pp. 4089- 4092 ,(1999) , 10.1016/S0040-4039(99)00656-5
D Gravel, S Benoît, S Kumanovic, H Sivaramakrishnan, On the palladium catalyzed reaction of methallyl-1,1-diacetate with cyclic β-ketoesters. Intervention of hidden mechanisms. Tetrahedron Letters. ,vol. 33, pp. 1403- 1406 ,(1992) , 10.1016/S0040-4039(00)91632-0
Rudolf Criegee, Oxydation ungesättigter Kohlenwasserstoffe mit Blei (4)‐salzen European Journal of Organic Chemistry. ,vol. 481, pp. 263- 302 ,(1930) , 10.1002/JLAC.19304810117
David W. Boykin, Russell L. Hertzler, John K. Delphon, Edmund J. Eisenbraun, Oxygen-17 NMR studies on alkylindanones: steric effects Journal of Organic Chemistry. ,vol. 54, pp. 1418- 1423 ,(1989) , 10.1021/JO00267A033
B. S. Hurlbert, B. F. Valenti, Condensed pyrimidine systems. XXIV. The condensation of 2,4,6-triaminopyrimidine with malondialdehyde derivatives Journal of Medicinal Chemistry. ,vol. 11, pp. 708- 710 ,(1968) , 10.1021/JM00310A016
J.S. Yadav, B.V.S. Reddy, P. Sreedhar, G. Kondaji, K. Nagaiah, Mild and efficient conversion of aldehydes to gem-diacetates using 2nd generation ionic liquids Catalysis Communications. ,vol. 9, pp. 590- 593 ,(2008) , 10.1016/J.CATCOM.2007.02.031
Leiv K. Sydnes, Marcel Sandberg, THE CHEMISTRY OF ACYLALS. PART I. THE REACTIVITY OF ACYLALS TOWARDS GRIGNARD AND ORGANOLITHIUM REAGENTS Tetrahedron. ,vol. 53, pp. 12679- 12690 ,(1997) , 10.1016/S0040-4020(97)00789-8
Xiyan Lu, Yujin Huang, Palladium-catalyzed reaction of nucleophiles with diacetates of allylic 1,1-diols Journal of Organometallic Chemistry. ,vol. 268, pp. 185- 190 ,(1984) , 10.1016/0022-328X(84)80246-6