SYNTHESIS AND DIELS-ALDER REACTIONS OF THIOISOBENZOFURANS

Citation
Jh. Bailey et al., SYNTHESIS AND DIELS-ALDER REACTIONS OF THIOISOBENZOFURANS, Journal of the Chemical Society. Perkin transactions. I, (5), 1995, pp. 589-592
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0300922X
Issue
5
Year of publication
1995
Pages
589 - 592
Database
ISI
SICI code
0300-922X(1995):5<589:SADROT>2.0.ZU;2-0
Abstract
Anions prepared by deprotonation of benzofused thionolactones reacted with alkylating agents preferentially on sulfur. The resulting isobenz ofurans underwent Diels-Alder reactions with dienophiles. This chemist ry was developed as a one-pot procedure for the synthesis of bridged p recursors of polycyclic aromatic compounds. The structure of one of th e adducts, dimethyl endo-1-methylsulfanyl-8-phenyl-11-oxatricyclo[6.2. 1.0(2,7)] Undeca-2,4,6-triene-9.10-dicarboxylate 5a, was determined b y single-crystal X-ray diffraction. The versatility of this approach w as extended by lithiation of the intermediate anion whereby alkylation introduced a further substituent on the aromatic nucleus. This method ology may be appropriate for the synthesis of anti-tumour prodrugs.