synthesis of some new mono- and bis-polycyclic aromatic spiro and bis-nonspiro-β-lactams合成一些新的mono -和bis-polycyclic芳斯皮罗和bis-nonspiro-β-lactams.pdf

Molecules 2010, 15, 515-531; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of Some New Mono- and Bis-Polycyclic Aromatic Spiro and Bis-Nonspiro-β-Lactams Aliasghar Jarrahpour * and Edris Ebrahimi Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran; E-Mail: edris.ebrahimi@ (E.E.) * Author to whom correspondence should be addressed; E-Mail: aliasghar6683@ or jarrah@susc.ac.ir; Tel.: +98-711-228-4822; Fax: +98-711-228-0926. Received: 2 November 2009; in revised form: 3 December 2009 / Accepted: 9 December 2009 / Published: 22 January 2010 Abstract: Some new mono-and bis-polycyclic aromatic spiro-β-lactams and bis-non spiro- polycyclic aromatic β-lactams have been synthesized from imines derived from anthracene-9-carbaldehyde, 2-naphtaldehyde and a ketene derived from 9H-xanthene-9- carboxylic acid and phenoxyacetic acid by a [2+2] cycloaddition reaction. The cycloadducts were characterized by spectral data, including 1H-NMR, 13C-NMR, IR and elemental analyses. The configurations of some of these mono-spiro-β-lactams were established by X-ray crystal analysis. Keywords: mono- and bis-spiro-β-lactam; polycyclic aromatic imine; 9H-xanthene-9- carboxylic acid; phenoxyacetic acid; [2+2] cycloaddition; tosyl chloride 1. Introduction β-Lactams, being a structural unit found in the most widely used antibiotics [1], have occupied a basic position i