synthesis of benzo[ ]fluorenone nuclei of stealthins合成苯并[]stealthins芴酮核.pdfVIP

Hindawi Publishing Corporation Research Letters in Organic Chemistry Volume 2009, Article ID 528081, 5 pages doi:10.1155/2009/528081 Research Letter Synthesis of Benzo[b]fluorenone Nuclei of Stealthins Sujit Kumar Ghorai, Saroj Ranjan De, Raju Karmakar, Nirmal Kumar Hazra, and Dipakranjan Mal Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India Correspondence should be addressed to Dipakranjan Mal, dmal@chem.iitkgp.ernet.in Received 3 December 2008; Accepted 16 February 2009 Recommended by Robert Strongin Two routes, one based on a Michael-initiated aldol condensation and the other on an intramoleculer carbonyl-ene reaction, have been found to be feasible for an entry to benzo[b]fluorenones. Reaction of 4,9-dimethoxybenz[f ]indenone with nitromethane in the presence of DBU gave the corresponding Michael adduct, which afforded 2-methyl-5,10-dimethoxybenzo[b]fluorenone on reaction with methacrolein under a variety of basic conditions. Similarly, 2-methallyl-4,9-dimethoxybenz[f ]indenone reacted with nitromethane to give the corresponding Michael adduct, Nef reaction of which furnished 3-formyl-2-methyl-4,9- dimethoxybenz[f ]indanone. This underwent ene-cyclization under the influence of SnCl4. 5H2O, and yielded 2-methyl-5,10- dimethoxybenzo[b]fluorenone. Copyright © 2009 Sujit Kumar Ghorai et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 1. Introduction different base-solvent systems (Scheme 1). But, none of the atte