One‐pot Synthesis of 3‐Aryliden‐2,3‐dihydro‐4‐quinolones from o‐Anilinopropargyl Alcohols via Aldol Condensation of in situ Generated 2,3‐Dihydroquinolin‐4‐ones and Aryl Aldehydes

Author(s):  
yan yin ◽  
Wanyong Pan ◽  
Jiulong Zhai ◽  
Hong Yang ◽  
Tiantian Li ◽  
...  
2020 ◽  
Vol 17 (10) ◽  
pp. 743-748
Author(s):  
Sultan Pathan ◽  
Anil Repale ◽  
Girdhar Pal

Celecoxib containing pyrazole derivatives were synthesized by path aldol condensation of substituted ketone with trifluoroethyl acetate subsequently by cyclization of the formed chalcones with 4-methanesulfonylphenylhydrazine. Here, a one-pot synthesis of celecoxib and substituted analogues have been reported which are nonsteroidal anti-inflammatory drugs for their cyclooxygenase (COX) inhibition, anti-inflammatory activity and ulcerogenic liability. In order to intermediate work-up, a continuous one-pot synthesis has been developed, performing the entire reaction sequence that results in a shorter time with good yield.


Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3221-3230 ◽  
Author(s):  
Wei Sun ◽  
Mingjuan Zhang ◽  
Peilang Li ◽  
Yiqun Li

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus–Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72–88%) under mild conditions.


2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.


Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...


Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee

Studies on a one-pot synthesis of novel multisubstituted 1-alkoxyindoles 1 and their mechanistic investigations are presented. The synthesis of 1 was successfully achieved through consecutive four step reactions from substrates 2. The substrates 2, prepared through a two-step synthetic sequence, underwent three consecutive reactions of nitro reduction, intramolecular condensation, and nucleophilic 1,5-addition to provide the intermediates, 1-hydroxyindoles 8, which then were alkylated in situ with alkyl halide to afford the novel target products 1. We optimized the reaction conditions for 1 focusing on the alkylation step, along with the consideration of formation of intermediates 8. The optimized condition was SnCl2·2H2O (3.3 eq) and alcohols (R1OH, 2.0 eq) for 1–2 h at 40 °C and then, base (10 eq) and alkyl halides (R2Y, 2.0 eq) for 1–4 h at 25–50 °C. Notably, all four step reactions were performed in one-pot to give 1 in good to modest yields. Furthermore, the mechanistic aspects were also discussed regarding the reaction pathways and the formation of side products. The significance lies in development of efficient one-pot reactions and in generation of new 1-alkoxyindoles.


Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.


2007 ◽  
Vol 40 (2) ◽  
pp. 191-198 ◽  
Author(s):  
Hakan Durmaz ◽  
Aydan Dag ◽  
Ozcan Altintas ◽  
Tuba Erdogan ◽  
Gurkan Hizal ◽  
...  

2011 ◽  
Vol 76 (11) ◽  
pp. 1307-1315 ◽  
Author(s):  
Behrooz Maleki ◽  
Hafezeh Salehabadi ◽  
Zeinalabedin Sepehr ◽  
Mina Kermanian

A simple and benign protocol has been explored for the preparation of 2,4,6-triarylpyridines by a one-pot reaction between aryl aldehydes, enolizable ketones and ammonium acetate in the presence of N-bromosuccinimide or trichloroisocyanuric acid as green and neutral catalysts. The reactions proceed smoothly at 130 °C under solvent-free conditions to provide 2,4,6-triarylpyridines in good yields.


Sign in / Sign up

Export Citation Format

Share Document