73053-85-7Relevant academic research and scientific papers
Indole heterocyclic compound, preparation method thereof and application of indole heterocyclic compound in prevention and treatment of plant diseases
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Paragraph 0046-0047; 0050, (2020/07/15)
The invention discloses an indole heterocyclic compound as well as a preparation method and application thereof in prevention and treatment of plant diseases. According to the method, indole is reacted with oxalyl chloride to obtain indole oxalyl chloride, then indole oxalyl chloride is reduced by tributylstannane to obtain indole carbonyl acetaldehyde, and finally indole carbonyl acetaldehyde isreacted with a corresponding amino acid under the catalysis of iodine to obtain a compound. The indole heterocyclic compound provided by the invention shows especially excellent plant virus resistingactivity, can well inhibit the tobacco mosaic virus, and also shows broad-spectrum plant pathogenic bacteria resisting activity.
First reported propylphosphonic anhydride (T3P) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
Szabó, Tímea,Dancsó, András,ábrányi-Balogh, Péter,Volk, Balázs,Milen, Mátyás
supporting information, p. 1353 - 1356 (2019/04/27)
In the present work, a propylphosphonic anhydride (T3P) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitri
Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus
Liu, Bin,Li, Rui,Li, Yanan,Li, Songyi,Yu, Jin,Zhao, Binfen,Liao, Ancai,Wang, Ying,Wang, Ziwen,Lu, Aidang,Liu, Yuxiu,Wang, Qingmin
, p. 1795 - 1806 (2019/02/27)
Plant viral diseases cause tremendous decreases in crop yield and quality. Natural products have always been a valuable source for lead discovery in medicinal and agricultural chemistry. A series of pimprinine alkaloids and their derivatives were prepared and identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). The antiviral activities of these alkaloids against tobacco mosaic virus (TMV) were systematically investigated for the first time. Most of the compounds exhibited higher antiviral activities than ribavirin. Compounds 5l, 9h, and 10h, which had similar or higher antiviral activities than ningnanmycin (perhaps the most widely used antiviral agent at present), emerged as new antiviral pilot compounds. This systematic structure-activity-relationship research lays the foundation for simplifying the structure of these alkaloids. The ring-open products, acylhydrazones 9a-9u, were also found to possess good antiviral activities. Moreover, all the synthesized compounds displayed broad-spectrum fungicidal activities. This study provides important information for the research and development of pimprinine alkaloids as novel antiviral agents.
A 5 - (3 - indolyl) - oxazole compound of preparation method
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, (2017/09/12)
The invention discloses a preparation method of a 5-(3-indolyl)-oxazole compound with a structure as shown in the formula (I). The method comprises the following step: in the presence of iodine and dimethyl sulfoxide, a compound with a structure as shown in the formula (II) and a compound with a structure as shown in the formula (III) undergo a contact reaction. Raw materials used in the preparation method are cheap and easily available. The preparation method is simple and the preparation step is short. In addition, the contact reaction can be carried out by a one kettle way during synthetic operation. Yield is high and can reach 84%. The preparation method provided by the invention is especially suitable for industrial production.
One-pot total synthesis: The first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids
Xiang, Jiachen,Wang, Jungang,Wang, Miao,Meng, Xianggao,Wu, Anxin
supporting information, p. 7470 - 7475 (2014/12/10)
In this work, we accomplished the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners: pimprinine, pimprinethine, pimprinaphine, WS-30581A, WS-30581B, laboradorin 1, uguenenazole, balsoxine, texamine in one-pot from commercially available starting materials including amino acids. Further investigating into the mechanism revealed that this improved transformation was achieved by the integration of iodination, Kornblum oxidation, condensation, decarboxylation, annulation, and oxidation reaction sequence.
Identification and isolation of insecticidal oxazoles from Pseudomonas spp.
Grundmann, Florian,Dill, Veronika,Dowling, Andrea,Thanwisai, Aunchalee,Bode, Edna,Chantratita, Narisara,Ffrench-Constant, Richard,Bode, Helge B.
supporting information; experimental part, p. 749 - 752 (2012/07/01)
Two new and five known oxazoles were identified from two different Pseudomonas strains in addition to the known pyrones pseudopyronine A and B. Labeling experiments confirmed their structures and gave initial evidence for a novel biosynthesis pathway of t
An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation
He, Weimin,Li, Chaoqun,Zhang, Liming
, p. 8482 - 8485 (2011/07/08)
The first efficient intermolecular reaction of gold carbene intermediates generated via gold-catalyzed alkyne oxidation has been realized using nitriles as both the reacting partner and the reaction solvent, offering a generally efficient synthesis of 2,5-disubstituted oxazoles with broad substrate scope. The overall reaction is a [2 + 2 + 1] annulation of a terminal alkyne, a nitrile, and an oxygen atom from an oxidant. The reaction conditions are exceptionally mild, and a range of functional groups are easily tolerated. With complex and/or expensive nitriles, only 3 equiv could be sufficient to achieve serviceable yields in the absence of any solvent and using only 1 mol % BrettPhosAuNTf2 as the catalyst.
A novel and short synthesis of naturally occurring 5-(3′-indolyl) oxazoles
Kumar, Dalip,Sundaree, Swapna,Patel, Gautam,Kumar, Anil
, p. 1425 - 1428 (2011/02/22)
A novel, concise, and convenient synthesis of 5-(3′-indolyl)oxazoles using relatively benign reagent [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo] benezene has been described. The advantages of this procedure include operational simplicity, good yield, and
A facile synthesis of naturally occurring 5-(3-indolyl)oxazoles
Kumar, Dalip,Sundaree, Swapna,Patel, Gautam,Rao
, p. 867 - 869 (2008/04/13)
A simple and efficient synthesis of naturally occurring 5-(3-indolyl)oxazoles is described. The key steps of this convergent approach are the formation of a 3-tosyloxyacetyl-1-benzenesulfonylindole, a 3-amino-acetyl-1-benzenesulfonylindole hydrochloride a
