Synthesis of new triphenodithiazine- and indolocarbazolediones of biological interest

Abstract

Tetrabromo-p-benzoquinone reacted with excess aromatic amines to give 2,5-dirylamino-3,6-dibromo-p-benzoquinones. The latter molecules on heating with sodium sulfide in alcohol in the presence of air gave triphenodithiazinediones. Heating with copper powder in nitrobenzene transformed these compounds into the respective indolocarbazolediones. Comparative antimicrobial and antifungal activities of the studied compounds were determined and discussed.

Recent advances in 1,4-benzoquinone chemistry

“…204 Tetrabromo-1,4-benzoquinone (164) reacted with excess aromatic amines (169) to give 2,5-diarylamino-3,6-dibromo-p-benzoquinones (170). On heating with sodium sulfate in alcohol in the presence of air gave triphendiazones (171).…”

Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

“…Substituted derivates of 59 were prepared by Youssef et al by reacting substituted anilines and tetrabromo- p- benzoquinone in a three step reaction. Also similar ring expanded systems were prepared by this method [47].…”

A convenient total synthesis of indolo[2,3‐b]carbazole‐6,12‐dione

“…Furthermore, some quinone derivatives exhibit good antibacterial [16,17] and antimalarial properties. New indolocarbazolediones possessing unique heterocyclic carbazole units fused with quinone moiety show interesting antimicrobial and antifungal activities [18]. In vivo degradation, the parent indolo [3,2-b]carbazole (3) and indolo [2,3-b]carbazole (4) acts as precursors leading to the formation of both indolocarbazolediones 1 and 2 respectively [14].…”

“…In vivo degradation, the parent indolo [3,2-b]carbazole (3) and indolo [2,3-b]carbazole (4) acts as precursors leading to the formation of both indolocarbazolediones 1 and 2 respectively [14]. Several reports [19] have been documented for the multistep synthesis of indolocarbazole alkaloids but very little information [14,18] is available on the synthesis of indolocarbazolediones. To date, there is only one report [14] on the synthesis of indolo [2,3-b]carbazole-6,12-diones using indole as a primary compound.…”

“…104 C; 1 H NMR (CDCl 3 , 500 MHz): δ H = 2.23 (t, 2H, C 3 -H), 2.64 (t, 2H, C 2 -H), 3.04 (t, 2H, C 4 -H), 5.82 (s, 2H, N-CH 2 ), 7.10-7.33 (m, 7H, ArH), 7.34 (s, 1H, ArH), 7.66 (d, J = 7.0 Hz, 1H, ArH). 13 C NMR (CDCl 3 , 125 MHz): δ C = 21.93, 24.74, 40.04, 47.94, 110.98, 120.33, 121.41, 125.10 (Â2), 126.78, 126.92, 127.14, 128.52 (Â2), 129.96, 129.99, 138.43, 139.45, 192.03.IR (KBr): ν 2937, 1649, 1615, 1498 cm À1 .HRMS (ESI, m/z): Calcd for C 19 H 18 NO [M + H] + 276.1383, found 276.1380.4.10 | 9-Benzyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazole-2-carbaldehyde(18)…”