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1.
Antonio Guirado Jos A. Sandoval Enrique Alarcn María Vera Delia Bautista Jesús Glvez 《Journal of heterocyclic chemistry》2019,56(6):1873-1878
The first synthetic approach to hitherto unknown 3‐aryl‐5‐dichloromethyl‐Δ2‐1,2,4‐oxadiazolines, of synthetic and biological interest, has been developed involving high‐yield reactions between N‐(2,2‐dichlorovinyl)benzimidoyl chlorides and hydroxylamine. The molecular structure of one member of this new family of compounds—5‐dichloromethyl‐3‐(4‐fluorophenyl)‐1,2,4‐oxadiazoline—has been determined by X‐ray crystallography. Density functional theory calculations supporting the proposed reaction pathway for the formation of these products have been carried out. 相似文献
2.
Construction of Hexahydropyrido[3,2‐c]carbazole and Hexahydropyrrolo[3,2‐c]carbazole Skeletons for the Synthesis of Related Indole Alkaloids
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Synthesis of tetracyclic hexahydropyrido[3,2‐c]carbazoles ( 9a and 9b ) and hexahydropyrrolo[3,2‐c]carbazoles ( 13a and 13b ) structures was achieved via a new synthetic approach for the synthesis of related indole alkaloids such as deethylaspidospermidine and deethylibophyllidine. Hexahydropyrrolo[3,2‐c]carbazole structure was constructed for the first time starting from ethyl 4‐oxo‐cyclohexanecarboxylate in seven steps. Some tetrahydrocarbazole derivatives ( 4 , 5 , 6 , 7 , 11 , and 12 ) were also synthesized. 相似文献
3.
Mustafa Göçmentürk Cevher Gündoğdu Hızlıateş Yavuz Ergün 《Journal of heterocyclic chemistry》2016,53(3):767-770
A new synthetic route for the synthesis of 5‐methyl‐6H‐pyrido[4,3‐b]carbazole ( 8 ), so‐called 11‐demethylellipticine, was described. Construction of the tetracyclic structure hexahydro‐1H‐pyrido[4,3‐b]carbazol‐5(6H)‐one skeleton ( 6 ) was also achieved by nucleophilic substitution reaction in the synthetic route. Also new tetrahydrocarbazole derivatives ( 2 , 3 , 4 , and 5 ) were synthesized. Several ellipticine analogs and octahydropyridocarbazole‐based G‐protein coupled receptors inhibitors can also be synthesized from tetracyclic structure ( 6 ) because of carbonyl functionality at position 5. 相似文献
4.
From‐Core and From‐End Direct CH Arylations: A Step‐Saving New Synthetic Route to Thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)‐Incorporated D‐‐π–A–π–D Functional Oligoaryls
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Po‐Han Lin Kuan‐Ting Liu Prof. Dr. Ching‐Yuan Liu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(24):8754-8757
In contrast to the traditional multistep synthesis, herein an efficient and fewer‐steps new synthetic strategy is demonstrated for the facile preparation of organic‐electronically important D–π–A–π–D‐type oligoaryls through sequential direct C?H arylations. This methodology has shown that the synthesis of thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)‐ or furano[3,4‐c]pyrrole‐4,6‐dione (FPD)‐centred target molecules could be accessed step‐economically either from the core structure (acceptor) or from the end structure (donor), which supplied a more flexible and succinct new synthetic alternative to the preparation of the π‐functional small‐molecule semiconducting materials. In addition, optical and electrochemical properties of the synthesized oligoaryls were examined. 相似文献
5.
A synthetic approach comprising several studied modifications was applied to the preparation of sn‐glycerol 1,2‐di‐γ‐linolenate 3‐palmitate ( 4 ). Thereby, a convenient and mild synthetic method was elaborated, affording 4 from 1,2‐O‐isopropylidene‐sn‐glycerol ( 1 ) in an average yield of 65 – 75% and analytically acceptable purity. 相似文献
6.
Suckchang Hong Myunggi Jung Yohan Park Min Woo Ha Cheonhyoung Park Dr. Myungmo Lee Prof. Dr. Hyeung‐geun Park 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(29):9599-9605
A new efficient and concise enantioselective synthetic method for (?)‐horsfiline is reported. (?)‐Horsfiline could be obtained from diphenylmethyl tert‐butyl malonate in 9 steps (32 %,>99 % ee) by using the enantioselective phase‐transfer catalytic allylation (91 % ee) as the key step. This approach can be applied as a practical route for the large‐scale synthesis of spirooxindole natural products, which enables a systematic investigation of their biological activity to be performed. 相似文献
7.
White KN Amagata T Oliver AG Tenney K Wenzel PJ Crews P 《The Journal of organic chemistry》2008,73(22):8719-8722
Our 2004 disclosure of the amino hemiketal-containing spiroleucettadine was met with keen interest by the natural products and synthetic communities. As repeated efforts to synthesize spiroleucettadine failed and questions regarding the original structure elucidation process arose, evidence mounted against the validity of the proposed structure. The low ratio of H/C in the core of spiroleucattadine complicated the original structure elucidation process. Speculation prompted a reisolation of spiroleucettadine from an untouched portion of the original Luecetta collection and a thorough analysis of analytical data. In addition, a systematic analysis of candidate structures was performed via density functional theory (DFT) calculations; a favored high scoring structure 1b was ultimately confirmed to be spiroleucettadine via X-ray analysis of crystalline spiroleucettadine and reinforced the validity of DFT calculations in structure elucidation. We present the revised structure of spiroleucettadine, a bicyclic sponge alkaloid with a scarcity of H-atoms in its core. 相似文献
8.
Silvana Guilardi Ruggiero Maria Teresa do Prado Gambardella Marcelo Cardoso Branco Antonio Jacinto Demuner Luis Claudio A. Barbosa Dorila Pil‐Veloso 《Acta Crystallographica. Section C, Structural Chemistry》2000,56(7):868-869
The crystal structure of 21α‐fluoro‐7‐norvouacapane‐17β,21α‐lactone, C20H25FO3, a new synthetic derivative of the diterpenoid 6α,7β‐dihydroxyvouacapan‐17β‐oic acid isolated from Pterodon polygalaeflorus Benth fruits, is described. 相似文献
9.
Copper‐Mediated Addition of Ethanolamine Affording 2‐Hydroxymethyl Naphtho[2,1‐d]oxazoles from 2‐Naphthols
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A new and mild synthetic approach was presented for the synthesis of naphtho[2,1‐d]oxazoles. In the presence of copper (II)‐ethanolamine, 2‐hydroxymethyl naphtho[2,1‐d]oxazoles were one‐pot synthesized in moderate to good yields through copper‐mediated oxidation of 2‐naphthols followed with the addition of ethanolamine in acetonitrile. 相似文献
10.
One‐Pot ‘On‐solvent’ Multicomponent Protocol for the Synthesis of Medicinally Relevant 4H‐Pyrano[3,2‐c]quinoline Scaffold
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Anatoly N. Vereshchagin Michail N. Elinson Ruslan F. Nasybullin Fedor V. Ryzhkov Sergey I. Bobrovsky Ivan S. Bushmarinov Mikhail P. Egorov 《Helvetica chimica acta》2015,98(8):1104-1114
‘One‐pot’ AcONa‐catalyzed transformation of salicylaldehydes, malononitrile and 4‐hydroxy‐1‐methylquinolin‐2(1H)‐one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2‐amino‐4‐(2‐hydroxyaryl)‐6‐methyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline‐3‐carbonitriles in 85–98% yields, which are potential pharmaceutical agents for treating disorders responsive to the induction of apoptosis, antiproliferation, or vascular disruption. This efficient ‘on‐solvent’ approach to the 4H‐pyrano[3,2‐c]quinoline scaffold represents a novel synthetic concept for multicomponent reaction (MCR) strategy and allows to combine the synthetic virtues of conventional MCR with ecological benefits and convenience of facile ‘on‐solvent’ procedure. 相似文献
11.
Copper‐Catalyzed Cascade Cyclization Reaction of 2‐Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H‐Benzotriazoles in Water
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Xiaobo Shang Shixian Zhao Prof. Dr. Wanzhi Chen Dr. Chao Chen Prof. Dr. Huayu Qiu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(7):1825-1828
A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed C?N coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of nitrene to N?N bonds. This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields. The procedure is simple and the starting materials and catalyst are easily available, offering a practical and convenient synthetic route to 2‐substituted benzotriazoles. 相似文献
12.
Vladimir T. Abaev Fatima A. Tsiunchik Alexander V. Butin Andrey V. Gutnov 《Journal of heterocyclic chemistry》2008,45(2):475-481
13.
The N‐glycans attached to some chloroviruses comprise a hyperbranched core structure without precedent. We are interested in the chemical synthesis of the hexasaccharide attached to ATCV‐1 (Acanthocystis turfacea Chlorella virus 1) for its distinct structure. After exploring four routes, the target hexasaccharide 2 was successfully synthesized for the first time in overall 10% yield over 8 steps from thioglycoside building blocks. This synthetic protocol is characterized by the three‐component one‐pot glycosylation and the regioselective glycosylation reactions. The disclosed synthetic approach to this new type of N‐glycans will facilitate the in‐depth understanding of their biological functions. 相似文献
14.
Alexander V. Butin Sergey K. Smirnov Tatyana A. Stroganova 《Journal of heterocyclic chemistry》2006,43(3):623-628
15.
2,3‐Dihydrothiophene 1,1‐dioxide (‘2‐sulfolene’) reacted with tosylmethyl isocyanide (TsMIC) in the presence of a base to give the hitherto unknown 3,5‐dihydro‐2H‐thieno[2,3‐c]pyrrole 1,1‐dioxide (‘β′‐sulfolenopyrrole’) from the expected cyclocondensation. A serendipitous formation of this β′‐sulfolenopyrrole was found earlier, when we investigated synthetic routes to a 3,5‐dihydro‐1H‐thieno[3,4‐c]pyrrole 2,2‐dioxide (a ‘β″‐sulfolenopyrrole’) from TsMIC and 2,5‐dihydrothiophene 1,1‐dioxide (‘3‐sulfolene’). Here, we present the synthesis and characterization of β′‐sulfolenopyrrole. The X‐ray crystal‐structure analyses of β′‐sulfolenopyrrole and the isomeric β″‐sulfolenopyrrole are also reported here. This β′‐sulfolenopyrrole is a new type of a functionalized pyrrole, which is likely to be of interest for pharmaceutical purposes. 相似文献
16.
Dr. Michael S. Klenov Alexey A. Guskov Dr. Oleg V. Anikin Prof. Dr. Aleksandr M. Churakov Dr. Yurii A. Strelenko Dr. Ivan V. Fedyanin Dr. Konstantin A. Lyssenko Prof. Dr. Vladimir A. Tartakovsky 《Angewandte Chemie (International ed. in English)》2016,55(38):11472-11475
This study presents the first synthesis and characterization of a new high energy compound [1,2,3,4]tetrazino[5,6‐e][1,2,3,4]tetrazine 1,3,6,8‐tetraoxide (TTTO). It was synthesized in ten steps from 2,2‐bis(tert‐butyl‐NNO‐azoxy)acetonitrile. The synthetic strategy was based on the sequential closure of two 1,2,3,4‐tetrazine 1,3‐dioxide rings by the generation of oxodiazonium ions and their intramolecular coupling with tert‐butyl‐NNO‐azoxy groups. The TTTO structure was confirmed by single‐crystal X‐ray. 相似文献
17.
The first synthetic approach to (±)‐Δ3‐2‐hydroxybakuchiol (=4‐[(1E,5E)‐3‐ethenyl‐7‐hydroxy‐3,7‐dimethylocta‐1,5‐dien‐1‐yl]phenol; 14 ) and its analogues 13a – 13f was developed by 12 steps (Schemes 2 and 3). The key features of the approach are the construction of the quaternary C‐center bearing the ethenyl group by a Johnson–Claisen rearrangement (→ 6 ); and of an (E)‐alkenyl iodide via a Takai–Utimoto reaction (→ 11 ); and an arylation via a Negishi cross‐coupling reaction (→ 12e – 12f ). 相似文献
18.
A series of new chiral 2(5H)‐furanone derivatives containing bis‐1,2,3‐triazole moiety were designed and synthesized from (5S)‐5‐alkoxy‐3,4‐dihalo‐2(5H)‐furanones 1 , dicarboxyl amino acids 2 , propargyl bromide, and organic azides 5 under mild conditions via the sequential three steps, including asymmetric Michael addition‐elimination, substitution and no‐ligand click reaction. Twelve new intermediates, including N‐[5‐alkoxy‐2(5H)‐furanonyl] dicarboxyl amino acids 3 and their corresponding propargyl esters 4 , and twelve target molecules 6 were characterized by FTIR, 1H NMR, 13C NMR, MS and elemental analysis. The influences of different synthetic conditions and substrates in each step were investigated. The research provides a new method and idea for the synthesis of 2(5H)‐furanone compounds with polyheterocyclic structure due to the diversities of four basic unit molecules. 相似文献
19.
Johny Wehbe Valrie Rolland Jean Martinez Marc Rolland 《Acta Crystallographica. Section C, Structural Chemistry》2003,59(8):o473-o475
The crystal and molecular structure of 1‐tert‐butyl 4‐ethyl (2′R,3′R,5′R,2S,3S)‐3‐bromomethyl‐3‐hydroxy‐2‐[(2′‐hydroxy‐2′,6′,6′‐trimethylbicyclo[3.1.1]hept‐3′‐ylidene)amino]succinate, C21H34BrNO6, is presented. This compound is an intermediate in the new synthetic route to β‐substituted β‐hydroxyaspartates, which are blockers of glutamate transport. 相似文献
20.
α,β‐Double Electrophilic Addition of Allene‐1,3‐Dicarboxylic Esters for the Construction of Polysubstituted Furans by KI/tert‐Butyl Hydroperoxide (TBHP)‐Promoted Oxidative Annulation
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Hong‐Liang Li Yu Wang Pei‐Pei Sun Prof. Dr. Xiaoyan Luo Prof. Dr. Zhenlu Shen Prof. Dr. Wei‐Ping Deng 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(27):9348-9355
An unprecedented KI/tert‐butyl hydroperoxide promoted tandem Michael addition/oxidative annulation of allene‐1,3‐dicarboxylic esters and 1,3‐dicarbonyl compounds has been developed. This procedure provides a new, facile, and transition‐metal‐free synthetic approach to afford polysubstituted furans in moderate to excellent yields (up to 93 %). This method first establishes a α,β‐double electrophilic reaction mode of allene‐1,3‐dicarboxylic esters to form 1,3‐dicarbonyl compounds. 相似文献