scholarly journals Functionalization of N-arylmaleimides by sp3 C–H bonds of hydroacridines(qinolines)

Author(s):  
N.V. Smetanin ◽  
◽  
A.V. Mazepa ◽  

The catalyst-free sp3 C–H functionalization of tetrahydroacridine(quinolines) derivatives has been achieved using a Michael-type reaction with N-arylmaleimides. This method enables the facile synthesis of biologically important N-aryl bearing tetrahydroacridine(quinolines) moieties in a single step with high yields. The reaction occurs under non-catalytic conditions by heating of hydroacridines(quinolines) in DMSO within 4 h at 100–1200C. The reaction between starting compounds allows synthesizing (3S/4R)-3-[(3R/4S)-9-chloroacridine(quinoline)-4-yl]-1(-N-aryl)pyrrolidine-2,5-diones with a good yield. The structure of compounds was proved by spectral methods of analysis. The 1H NMR spectrum shows characteristic signals of protons of the CH-groups in acridine(quinoline) (3.4–3.5 ppm) and pyrrolidine (3.8–3.9 ppm) cycles. It is interesting to note that the main direction of the fragmentation is the Michael retro-reaction, which is accompanied by the elimination of 1-(2-nitrophenyl)-1H-pyrrole-2,5-dione and leads to the formation of m/z ions of starting chloroacridines(quinolines).

2007 ◽  
Vol 61 (2) ◽  
Author(s):  
E. Gladkov ◽  
S. Sirko ◽  
B. Khanetskii ◽  
E. Lukinova ◽  
S. Desenko

AbstractNumber of novel derivatives of dihydrotriazolo-and-tetrazolopyrimidines containing carboxamide group in position 6 were obtained by multicomponent Biginelli-type reaction. The structures of all synthesized compounds were proved by NMR and MS spectral methods. The method of three-component Biginelli-type reaction is well suited for the synthesis of new promising dihydroazolopyrimidines providing a scaffold for screening of biological activity.


2017 ◽  
Vol 58 (15) ◽  
pp. 1490-1494 ◽  
Author(s):  
Rodrigo Abonia ◽  
Juan C. Castillo ◽  
Alexander Garay ◽  
Braulio Insuasty ◽  
Jairo Quiroga ◽  
...  

2020 ◽  
Author(s):  
XIAOLIN LIU ◽  
Xin Liang ◽  
YUBING HU ◽  
Qing Qu ◽  
Dongming Liu ◽  
...  

Catalyst-free spontaneous polymerization for the synthesis of halogen-rich polysulfonates at room temperature in air with 100% atom economy in high yields was developed. The resulting polymers possess various properties, including post-functionalization, extraordinarily high refractive index, visible photodegradation, photoacid generation, multi-color and 3D fluorescent photopatterning, and practical broad-spectrum antibacterial activity.


2020 ◽  
Author(s):  
XIAOLIN LIU ◽  
Xin Liang ◽  
YUBING HU ◽  
Qing Qu ◽  
Dongming Liu ◽  
...  

Catalyst-free spontaneous polymerization for the synthesis of halogen-rich polysulfonates at room temperature in air with 100% atom economy in high yields was developed. The resulting polymers possess various properties, including post-functionalization, extraordinarily high refractive index, visible photodegradation, photoacid generation, multi-color and 3D fluorescent photopatterning, and practical broad-spectrum antibacterial activity.


2016 ◽  
Vol 18 (4) ◽  
pp. 1032-1037 ◽  
Author(s):  
Jian Xiao ◽  
Hao Wen ◽  
Liang Wang ◽  
Lubin Xu ◽  
Zhihui Hao ◽  
...  

An efficient dehydrative SN1-type reaction of indolyl alcohols with diverse nucleophiles was developed using water as the solvent, affording versatile 3-indolyl derivatives in high yields. The advantages of being catalyst-free, environmentally benign, and wide substrate scope make it a promising method for preparation of indolyl compounds.


RSC Advances ◽  
2014 ◽  
Vol 4 (95) ◽  
pp. 53188-53191 ◽  
Author(s):  
Zhuzhou Shao ◽  
Liang Wang ◽  
Lubin Xu ◽  
Huaili Zhao ◽  
Jian Xiao

A facile catalyst-free tandem sp3 C–H functionalization/decarboxylation of 4-oxo-4H-chromene-3-carboxylic acid with 2-alkylazaarenes was developed, which can construct the biologically significant azaarene 2-substituted chromanones in a single step.


2018 ◽  
Vol 16 (1) ◽  
pp. 34-39
Author(s):  
Yao-Wei Li ◽  
Pei-Ming Zhang ◽  
Rui Li ◽  
Yan Bai ◽  
Yu Yu ◽  
...  

CDI combined with CH3SO3H was found to be highly effective for the cyclization of 2-aminothiophenol derivatives with carboxylic acids under MW condition. Fourteen benzothiazole derivatives were synthesized in good yield and their structures were characterized by 1H-NMR, 13CNMR, IR and mass spectrometry. This simple, rapid synthetic method is believed to provide a useful process for the synthesis of 2-substituted benzothiazole compounds.


2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.


2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Lukas Rieder ◽  
Katharina Ebner ◽  
Anton Glieder ◽  
Morten Sørlie

Abstract Background Lytic polysaccharide monooxygenases (LPMOs) are attracting large attention due their ability to degrade recalcitrant polysaccharides in biomass conversion and to perform powerful redox chemistry. Results We have established a universal Pichia pastoris platform for the expression of fungal LPMOs using state-of-the-art recombination cloning and modern molecular biological tools to achieve high yields from shake-flask cultivation and simple tag-less single-step purification. Yields are very favorable with up to 42 mg per liter medium for four different LPMOs spanning three different families. Moreover, we report for the first time of a yeast-originating signal peptide from the dolichyl-diphosphooligosaccharide-protein glycosyltransferase subunit 1 (OST1) form S. cerevisiae efficiently secreting and successfully processes the N-terminus of LPMOs yielding in fully functional enzymes. Conclusion The work demonstrates that the industrially most relevant expression host P. pastoris can be used to express fungal LPMOs from different families in high yields and inherent purity. The presented protocols are standardized and require little equipment with an additional advantage with short cultivation periods.


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