Expedited Synthesis of Substituted Dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones Structurally Related to Granulatimide

Abstract

Dipyrrolo[3,carbazole-1,3,4,6-tetraones can be considered as granulatimide analogues. In view of structure-activity relationship studies in these series, a parallel liquid-phase microwave-assisted synthesis was developed to generate a small library of compounds bearing various substituents at positions 8, 9, 10, or 11 on the aromatic framework.

Diels-Alder reactions of 1-amino-1,3-dienes and related systems

“…The one-pot reaction was performed starting from indoles and quinolinetriones 482 to give after regioselective Michael and DA reactions polycyclic carbazole derivatives 484 (Scheme 119). Indolylmaleimides 485 were prepared in two steps by Michael addition of indoles to maleimides followed by dehydrogenation using DDQ [306][307][308]. Prudhomme and co-workers [306][307][308][309][310][311][312][313][314][315] have studied the synthesis of bis-imide granulatimide analogues in order to evaluate in vitro antiproliferative activities and ChK1 inhibitory properties.…”

“…Indolylmaleimides 485 were prepared in two steps by Michael addition of indoles to maleimides followed by dehydrogenation using DDQ [306][307][308]. Prudhomme and co-workers [306][307][308][309][310][311][312][313][314][315] have studied the synthesis of bis-imide granulatimide analogues in order to evaluate in vitro antiproliferative activities and ChK1 inhibitory properties. DA reactions of compounds 485 with maleimide gave a compound, which after oxidation gave bis-imide granulatimide analogues 486 (Scheme 119) [306][307][308][309][310].…”

“…Prudhomme and co-workers [306][307][308][309][310][311][312][313][314][315] have studied the synthesis of bis-imide granulatimide analogues in order to evaluate in vitro antiproliferative activities and ChK1 inhibitory properties. DA reactions of compounds 485 with maleimide gave a compound, which after oxidation gave bis-imide granulatimide analogues 486 (Scheme 119) [306][307][308][309][310]. Similar DA reaction has been performed with lactam derivatives 487 and 488 by reaction with maleimides providing products 489 and 490, respectively [309].…”