ChemInform Abstract: SYNTHESIS OF 5‐HYDROXY‐1,2‐DIPHENYLINDOLE DERIVATIVES

Abstract

Aus β,p‐Bromanilinozimtsäureester wird mit Benzochinon (Ia) erhalten, das bei der Benzoylierung (Ib) ergibt.

Design, Synthesis and Biological Evaluation of N-phenylindole Derivatives as Pks13 Inhibitors againstMycobacterium tuberculosis

“…Ethyl (Z)-3-amino-3-(4-methoxyphenyl) acrylate (11) tained from ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (10) with ammonium for refluxing ethanol. The indole derivative (12) was formed from Compound 11 th Nenitzescu reaction with 1,4-benzoquinone catalyzed by ZnBr2 and the subseque nich reaction with 37% aqueous formaldehyde and piperidine to yield Compo [25,26]. Compound 14 was obtained from 13 via demethylation by boron tribromi ilarly, Compounds 15-20 were prepared in similar methods described above.…”

“…1 H NMR (400 MHz, CD 3 OD:CDCl 3 = 1:3) δ 7.41-7.32 (m, 3H), 7.12 (d, J = 6.5 Hz, 2H), 7.07 (d, J = 8.9 Hz, 1H), 7.01 (d, J = 7.9 Hz, 2H), 6.86 (d, J = 8.9 Hz, 1H), 6.76-6.68 (m, 2H), 4.44 (s, 2H), 3.53-3.34 (m, 2H), 3.21 (q, J = 7.1 Hz, 2H), 3.07-2.96 (m, 2H), 2.15-1.71 (m, 6H), and 0.87 (t, J = 7.2 Hz, 3H). 13 This compound was obtained from ethyl acetoacetate (26), aniline, employing Method D. Yield 47%; dark brown solid. 1 H NMR (400 MHz, DMSO-d 6 ) δ 9.29 (s, 1H), 7.67-7.54 (m, 3H), 7.48-7.41 (m, 2H), 7.19 (s, 1H), 6.90 (d, J = 7.8 Hz, 1H), 6.65 (d, J = 7.8 Hz, 1H), 4.31 (q, J = 6.8 Hz, 2H), 2.48 (s, 3H), and 1.38 (t, J = 6.8 Hz, 3H).…”

Methods for the Synthesis of Isogramines and Their Chemical Properties. (Review)

“…Of course, the only possibility for 1,2,3,6-tetrasubstituted [46][47][48][49][50][51][52] and 1,2,3,6,7-pentasubstituted [18] 5-hydroxyindoles is dimethylaminomethylation at position 4. This method was used for the synthesis of arbidol, labelled with C 14 at position 2 and at the ethoxycarbonyl group, in order to study its pharmacokinetics [53].…”

Synthesis of three Tricholoma-derived indoles via an ortho-quinone methide

“…Upon treating Mannich base 7 with sodium borohydride in ethanol at reflux, the desired product 8 was isolated. In this instance, thermal generation of the o-QM is followed by reduction/aromatization 12 to give the indole 8 bearing a methyl group at C4. Selective O-methylation of 8 gave the natural product 5-methoxy-2,4-dimethylindole 1, a key intermediate in our ongoing efforts towards the synthesis of sciodole (4).…”