Tetrahedron letters

Synthesis of indeno [1, 2-b] indole by flash vacuum pyrolysis of 2-phenylquinoline-3, 4-dicarboxylic anhydride

RFC Brown, KJ Coulston, FW Eastwood, MR Moffat

Index: Brown; Coulston; Eastwood; Moffat Tetrahedron Letters, 1991 , vol. 32, # 6 p. 801 - 802

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Citation Number: 6

Abstract

Flash vacuum pyrolysis of 2-phenylquinoline-3,4-dicarboxylic anhydride at 800°C/0.06 Torr. gave indeno[1,2- ]indole. This was reduced to form 5,10-dihydroindeno[1,2-b]indole and it added nucleophiles to give dihydroindenoindoles with the 10-substituents Ph, NEt 2 , OMe, Me, CH(COOMe) 2 , and CMe 2 NO 2 . ... Molecular ion, m/z 203.073 ± 0.002: C 15 H 9 N requires 203.073. ν max . (Nujol) 1626 w, 1605 w cm −1 . 1 H nmr spectrum, δ (CDCl 3 , 200MHz) ...

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