ChemInform Abstract: One‐Pot Conversion of 1‐Bromo‐β‐carboline and 1‐Bromocarbazole into Pentacyclic Compounds by Suzuki Cross‐Coupling Followed by Spontaneous Cyclization.

Abstract

One-Pot Conversion of 1-Bromo--carboline and 1-Bromocarbazole into Pentacyclic Compounds by Suzuki Cross-Coupling Followed by SpontaneousCyclization. -The regioisomer of (VII), 3-formylthiophene-2-boronic acid, fails to give defined products. -(GEHRING, A. P.; TREMMEL, T.; BRACHER*, F.; Synthesis 46 (2014) 7, 893-898, http://dx.

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…The 8 H -indolo­[3,2,1- de ]­phenanthridin-8-one ( C49.1 , Chart ) and 8 H -indolo­[3,2,1- de ]­acridin-8-one ( C49.2 ) ring systems are of interest because of their structural relationship to alkaloids of the canthine family . Several syntheses of the parent C49.1 and its substituted derivatives were described, starting from the 1930s work of Plant and Tomlinson, , followed by contributions from Teitei, and Ghosh et al More recent work from Gómez-Lor and Echavarren, Bracher et al, Wiczk et al, and Xu, Yao, et al explored several synthetic approaches to C49.1 , employing different disconnections of the fused framework. Various aza-analogues of C49.1 , containing additional embedded nitrogens and, occasionally, additional fused rings, were reported by Berti et al, Shipchandler and Mitscher, Desarbre and Merour Markgraf et al, Poupon et al, Dang and Stadlbauer, Huet et al, , Sarragiotto et al,and Bracher et al. , Related lactam derivatives were synthesized by Ziegler et al ( C49.5 ), Wolfbeis ( C49.6 ), and Stadlbauer et al ( C49.7 ) .…”

“…Several syntheses of the parent C49.1 and its substituted derivatives were described, starting from the 1930s work of Plant and Tomlinson, , followed by contributions from Teitei, and Ghosh et al More recent work from Gómez-Lor and Echavarren, Bracher et al, Wiczk et al, and Xu, Yao, et al explored several synthetic approaches to C49.1 , employing different disconnections of the fused framework. Various aza-analogues of C49.1 , containing additional embedded nitrogens and, occasionally, additional fused rings, were reported by Berti et al, Shipchandler and Mitscher, Desarbre and Merour Markgraf et al, Poupon et al, Dang and Stadlbauer, Huet et al, , Sarragiotto et al,and Bracher et al. , Related lactam derivatives were synthesized by Ziegler et al ( C49.5 ), Wolfbeis ( C49.6 ), and Stadlbauer et al ( C49.7 ) . Compound C49.2 was first reported by Eckert et al in 1922, and its chemistry was subsequently investigated by Hayashi, , Gilman et al, Hellwinkel and Melan, and Brown, Eastwood, et al Aza-analogues C49.3 and C49.4 were reported, respectively, by Molina et al and Puzik and Bracher …”

Discovery of a Selective Allosteric Inhibitor Targeting Macrodomain 2 of Polyadenosine-Diphosphate-Ribose Polymerase 14

“…Synthesis of GeA-69, MnK2−13, and MnK2−68. GeA-69, N-[3-(9H-carbazol-1-yl)pyridin-4-yl]acetamide, was prepared from known 37 1-bromocarbazole by a Suzuki cross-coupling procedure as follows: 74 mg (0.30 mmol) of 1-bromo-9H-carbazole, 61 mg (0.31 mmol) of 2-acetamidophenylboronic acid, and 39 mg (0.034 mmol) of Pd(Ph 3 P) 4 were placed in a microwave vial under a nitrogen atmosphere. A mixture of 3 mL of 1,2-dimethoxyethane and 2 mL of ethanol, previously degassed by purging with for 10 min with nitrogen, was added.…”