New Route to 20-Deethyldasycarpidone by Ring-Closure with DDQ

Uludag, Nesimi; Sanda, Mustafa; Asutay, Oktay; Coşkun, Necdet

doi:10.1080/00304948.2014.963458

Cited by 19 publications

(7 citation statements)

References 35 publications

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“…Alternatively, 2-(3-ethyl-1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetonitrile ( 1 ) allows direct synthetic route to the amide ( 2) [ 35 , 36 ]. Thus the amide was obtained in one step from the nitrile, due to its simplicity and only in a one-step, this synthesis of the amide improves those previously reported [ 37 ]. Such a strategy has never been applied in the synthesis of noruleine and uleine.…”

Section: Introductionsupporting

confidence: 66%

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

Uludag¹,

Üstün²,

Serdaroğlu³

2022

Heliyon

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Section: Introductionsupporting

confidence: 66%

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

Uludag¹,

Üstün²,

Serdaroğlu³

2022

Heliyon

Self Cite

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“…The (2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino [4,3-b]indole ring system of intermediate 7 is a structural feature of indole alkaloid families which is characterized by the presence of the 1,5-methanoozocino [4,3,b]indole moiety bearing (2,2-dimethoxyethyl) at N-2 position and the ring system of the strychnos alkaloids [1]. Multi-functionalized 1,5-methanoozocino [4,3,b]indole tetracyclic skeleton is very important for synthetic organic chemistry and is found in many different types of natural products, such as uleine [2], epidasycarpidone [3], 20-deethyldasycarpidone [4], 20-diethyl-4-demethyldasycarpidone [5]. These natural products, which possess a wide variety of biological properties, anti-HIV, antitumor, analgesia behavior [6].…”

Section: Introductionmentioning

confidence: 99%

New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole and DFT investigation

Uludag

Serdaroğlu

2020

Heliyon

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Development of efficient sequences for the synthesis of the title compound (2-(2,2-dimethoxyethyl)-1,2, 3,4,5,6hexahydro-1,5-methanoazocino[4,3-b]indole) (7) was described. The title compound was synthesized through several steps starting from phenylhydrazine hydrochloride and dimethyl (R)-2-(3-oxocyclohexyl)malonate. In this route, all synthesized compounds were observed by spectroscopic tools (FT-IR, NMR): 3,4,5,6,7-hexahydro-1H-1,5-methanoazocino[4,3-b]indole (7). The central step in these syntheses is the dehydrogenative reaction, which constructs the tetracyclic ring system from a much simpler tetracyclic precursor. The six-stable conformers of the compound (7) were used for further calculations such as FT-IR, NMR, NLO, and FMO analyses, performed at the B3LYP/6-311þþG(d,p) level. This work revealed that (7) can be a good material to use in the non-linear optical material because its β tensor is greater ten times than that of the urea.

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“…[35] Previously we reported the synthesis of strychnos alkaloids using a DDQ cyclization reaction. [36] In this study, we introduce a novel mechanism involving DDQ-catalyzed oxidative coupling between ketoximes and DEAD "diethyl acetylene dicarboxylate", paving the way for the synthesis of diversely substituted pyrroles (Scheme 1). [37] This work evaluated the bioavailability indexes of compounds Ph-F, Ph-Cl, Ph-Br, Ph-I, Ph-NO 2 , and Ph-tBC after electronic and spectroscopic characterization.…”

Section: Introductionmentioning

confidence: 99%

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

Serdaroğlu,

Uludağ,

Üstün

2024

ChemistrySelect

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The construction of pyrroles is an important heterocyclic group comprising many compounds with interesting properties that have led to numerous applications in various fields. We delineate a new synthetic method for the rapid construction of tree‐substituted pyrroles from readily available ketoximes as starting materials and also a new mechanism and method has been proposed. It is presented that substituted pyrroles were efficiently synthesized in high yields (up to 81 % yield) through the cyclization reaction of starting ketoximes mediated by 2,3‐dichlor‐5,6‐dicyanobenzoquinone (DDQ). Utilizing this protocol various pyrrole derivatives were synthesized from diethyl acetylene dicarboxylate (DEAD). We then developed the dehydrogenation reaction mechanism of this formation, also studied in detail, also all synthesized compounds were analyzed in detail by spectroscopic techniques (FT‐IR, 1H NMR, 13CNMR) which were compared with the computational data estimated at B3LYP/6‐311G** level. The thermochemical and electronic properties of the pyrroles were evaluated after optimizing and then confirming the equilibrium structures. ADMT scores were also considered to estimate/elucidate the possible bioavailability tendencies as well as the toxicity. In addition, the interactions of the optimized molecules were evaluated by molecular docking methods against BSA “Bovine Serum Albumin” and LIF “Leukemia Inhibitory Factor”. The results obtained from this study will ideally provide a fundamental source in contemporary drug design in terms of both the key electronic properties underlying the possible reactivity features and toxicity.

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New Route to 20-Deethyldasycarpidone by Ring-Closure with DDQ

Cited by 19 publications

References 35 publications

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

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

New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole and DFT investigation

Advancing Pyrrole Synthesis through DDQ Catalysis: A Comprehensive Research Incorporating DFT, ADMT, and Molecular Docking Analysis

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