scholarly journals One-pot synthesis of tetracyclic fused imidazo[1,2-a]pyridines via a three-component reaction

2016 ◽  
Vol 12 ◽  
pp. 1487-1492 ◽  
Author(s):  
Bo Yang ◽  
Chuanye Tao ◽  
Taofeng Shao ◽  
Jianxian Gong ◽  
Chao Che

A novel three-component reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo[1,2-a]pyridines in a one-pot fashion utilizing readily available 2-aminopyridines, isatins and isocyanides. The three-component coupling proceeds through the Groebke–Blackburn–Bienaymé reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reaction of the in-situ generated imidazo[1,2-a]pyridines bearing an isocyanate functional group.

2014 ◽  
Vol 4 (11) ◽  
pp. 4001-4009 ◽  
Author(s):  
Bibek Jyoti Borah ◽  
Subrat Jyoti Borah ◽  
Kokil Saikia ◽  
Dipak Kumar Dutta

Size selective Au0-nanoparticles were generatedin situin the nanopores of montmorillonite and applied in the one-pot, three-component coupling of an aldehyde, an amine and an alkyne to synthesize propargylamines.


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.


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.


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...


Molbank ◽  
10.3390/m1236 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1236
Author(s):  
Yordan Stremski ◽  
Stela Statkova-Abeghe

An convenient one-pot approach for the synthesis of new (E)-2-(2-oxo-4-phenylbut-3-en-1-yl)benzo[d]thiazole-3(2H)-carboxylates is demonstrated. The method is based on a three-component reaction of benzylideneacetone with electrophilic N-alkoxycarbonylbenzothiazolium species formed in situ. The newly synthesized compounds were fully characterized by 1D 1H, 13C- NMR, IR and MS.


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.


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

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