A SIMPLE AND EFFICIENT METHOD FOR CONSTRUCTING AZOCINO[4,3-b]INDOLE

A new synthetic procedure has been developed to prepare the biologically important azocino[4,3-b]indole via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tetrahydrocarbazole derivative bearing an amide side chain at the C-2 position. For the first time, this strategy is based on a different method for the C-2 position of the tetrahydrocarbazole for the synthesis of methanoazocino[4,3-b]indole. The notable features of this protocol include its operational simplicity and high reaction yields. Furthermore, the structures of all the presently synthesized compounds were confirmed using spectroscopic methods (1H NMR, 13C NMR, FT-IR). © 2022,Macedonian Journal of Chemistry and Chemical Engineering.All Rights Reserved.Tekirdağ Namık Kemal Üniversitesi, TNKUThe author thanks Namık Kemal University for analysis of our article structure

A new approach to the total synthesis of (±)-nordasycarpidone by ring-closure with tetrachloro-1,4-benzoquinone

new synthetic route for the (±)-nordasycarpidone was achieved in five steps with an overall yield of 41 %. This route involves ring closure and formation of 5 which has a methanoazocino[4,3-b]indole skeleton in the key step. The reaction also involved a cyclization reaction of tetrahydrocarbazole with a monoalkyl nitrile side chain at the C-2 position, and this reaction was mediated by tetrachloro-1,4-benzoquinone (TCB). The central step in the synthesis was the closure of the D-ring of the intra-molecu-lar structure and the addition of amine, which resulted in an aza-tetracyclic substructure that contained the ABCD-ring of the strychnos alkaloid family. © 2020, Macedonian Journal of Chemistry and Chemical Engineering.The author wish thanks must go to Prof. Dr. Tuncer Hokelek for continuous support in the preparations and writing of this work. The author is also grateful to Namik Kemal University for the analysis of the synthesized compounds

Bazı o-Hidroxsi Enaminon Türevlerinin ve Siklohekzadienin Tetrachloro-1,4-benzoquinone (TCB) Ortamında Tandem Oxidative-Reaksiyonu ile Sentezi

Bu çalışmada 7 adet orjinal o-hidroksi aril enaminon ile siklohekzadienin türevleri TCB ortamında tandem reaksiyonu ile sentezlenip, yapıları 1H NMR, 13C NMR ve HR-MS spektroskopisi aydınlatılmıştır. Ayrıca, bu reaksiyon oxidatif birleşme ve molekül içi halkalaşma tepkimesini içermektedir. Kromonlar, doğal olarak oluşan bileşiklerden meydana gelen bir gruptur. Doğada, özellikle bitkilerin bileşenleri içerisinde bulunur. Halkalı kromonların yaygın olarak doğal biyolojik aktif özelliklere sahip olmasından dolayı, literatüre giren her kromon türevlerinin sentezi literatüre önemli katkı yapacağı düşünülmektedir. Bu çalışmada sentezlenen söz konusu bileşiklerin yüzdesel verimleri oldukça yüksek değerlere sahip olup, oda sıcaklığında ılımlı şartlarda gerçekleştirilmiştir

A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide

This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic. © 2019 Editura Academiei Romane. All rights reserved.Acknowledgements. This work was supported by Tekirdag Namık Kemal University and this research also is part of Ozge Nur Giden’s MSc thesis

Strychnos alkaloids: total synthesis, characterization, DFT investigations, and molecular docking with AChE, BuChE, and HSA

An efficient five steps, the protection-deprotection synthetic a novel synthetic routes to(+/-) noruleine (f)-uleine, are reported starting from tetrahydrocarbazole fused monoalkyl nitrile at C-2 position that is prepared on mul-tigram scale from 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetonitrile (1) as well as the key azocino [4,3-b]indole skeleton is constructed via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tet-rahydrocarbazole derivative possessing direct amide synthesis from nitrile. As a result, Total synthesis of nor-uleine and uleine has been developed, which is accomplished in 4 and 5-steps synthesis of the ABCD tetracyclic of the strychnos alkaloids with an overall yield of 44% and 39%, respectively. The DFT computations were per-formed with B3LYP/6-311g(d,p) level to determine inter and intramolecular interactions and reactivity features of the compound 3-6. Also, TD-DFT computations were performed to characterize the electronic absorption spectra of all compounds. Last, the interactions of compounds 3-6 with selected targets AChE, BuChE, and HSA were evaluated in light of the molecular dockings. The bioactivity and drug-likeness scores revealed that com-pound 6 3-6 can be proper candidate for future drug-design studies more than the other compounds.Scientific and Technological Research Council of Turkey [TUBITAK] [112T503]Nesimi Uludag was supported by Scientific and Technological Research Council of Turkey [TUBITAK Project No.112T503]

2+2] cycloadditions in polar and non-polar solvents

In this study, enamines of cyclic ketones reacting with methyl acetylenecarboxylate to produce intermadiate cyclobutene adducts have been isolated. Reactions of methyl acetylenecarboxylate with enamines derived from cyclobutene adducts and ring expansion products were described

5-(3,6-Dibromo-9H-carbazol-9-yl)penta­nenitrile

In the title compound, C17H14Br2N2, the carbazole skeleton is nearly planar [maximum deviation = 0.055 (2) Å]. In the crystal, aromatic π–π stacking is observed between parallel carbazole ring systems of adjacent mol­ecules, the shortest centroid–centroid distance between benzene rings being 3.4769 (11) Å

9-(4-Nitro­phenyl­sulfon­yl)-9H-carbazole

In the title mol­ecule, C18H12N2O4S, the carbazole skeleton is nearly planar [maximum deviation = 0.037 (1) Å] and is oriented at a dihedral angle of 73.73 (5)° with respect to the benzene ring. An intra­molecular C—H⋯O hydrogen bond links a nitro O atom to the carbazole skeleton. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. π–π contacts between inversion-related benzene rings [centroid–centroid distance = 3.7828 (8) Å] and two weak C—H⋯π inter­actions may also stabilize the structure

9-Benzyl-9H-carbazole

The asymmetric unit of the title compound, C19H15N, contains two crystallographically independent mol­ecules. In both mol­ecules, the planar carbazole moieties [maximum deviations = 0.037 (4) and 0.042 (3) Å] are oriented with respect to the adjacent benzene rings, at dihedral angles of 85.29 (8) and 89.89 (7)°, respectively. In the crystal structure, weak C—H⋯π inter­actions are observed involving the carbazole rings

An Efficient Synthesis of Nitriles from Aldoximes in the Presence of Trifluoromethanesulfonic Anhydride in Mild Conditions

A new and convenient protocol has been proposed for the transformation of aldoximes to nitriles using trifluoromethanesulfonic anhydride and triethylamine. The proposed method allows a range of aldoximes, including aromatic, heterocyclic, aliphatic, and cycloaliphatic aldoximes, to be converted to the corresponding nitriles in good to excellent yields.Namik Kemal University Scientific Research Projects Coordination DepartmentNamik Kemal University [NKUBAP.00.10, YL.14.06]The study was performed under financial support by the Namik Kemal University Scientific Research Projects Coordination Department (project no. NKUBAP.00.10. YL.14.06)