scholarly journals Deoxygenative C2-heteroarylation of quinoline N-oxides: facile access to α-triazolylquinolines

2021 ◽  
Vol 17 ◽  
pp. 485-493
Author(s):  
Geetanjali S Sontakke ◽  
Rahul K Shukla ◽  
Chandra M R Volla

A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available N-oxides and N-sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.

2017 ◽  
Vol 15 (33) ◽  
pp. 6997-7007 ◽  
Author(s):  
Anirban Kayet ◽  
Vinod K. Singh

Pd(ii)–Ag(i) catalysed, highly efficient synthesis of diindolylmethanes under mild reaction conditions, with six new bonds being formed in a one-pot fashion, and the products being transformed into synthetically useful compounds.


2016 ◽  
Vol 14 (1) ◽  
pp. 122-130 ◽  
Author(s):  
Deuk-Young Goo ◽  
Sang Kook Woo

We have developed a highly efficient synthetic route to carbazoles that employs sequential C–C/C–N bond formation via Suzuki cross-coupling and Cadogan cyclization. The developed method is compatible with electron neutral, rich or deficient substrates. The synthetic utility of this method was demonstrated by the concise syntheses of four natural products.


Synthesis ◽  
2021 ◽  
Author(s):  
Keyin Ye ◽  
Jun-Fa Han ◽  
Peng Guo ◽  
Lin Chen

A highly efficient cobalt-catalyzed homocoupling of terminal alkynes with di-tert-butyldiaziridinone as the oxidant has been developed. The protocol tolerates a wide array of terminal alkynes, both activated and unactivated alkynes, to afford their corresponding conjugated 1,3-diynes. The mild reaction conditions further allow late-stage homocoupling of alkynes derived from complex natural products.


2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Shubha Jain ◽  
Deepika Rajguru ◽  
Balwant S. Keshwal ◽  
Aman D. Acharya

A rapid, clean, and highly efficient method for synthesis of dihydropyrano[3,2-c]chromene derivatives by one-pot, three-component condensation of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin using DABCO as catalyst in solvent-free neat conditions is described. The present method has the advantages of mild reaction conditions, short reaction times, easy isolation of products, and excellent yields.


2017 ◽  
Vol 58 (2) ◽  
Author(s):  
Behrooz Maleki ◽  
Samaneh Sedigh Ashrafi

<p>The rapid and environmental synthetic route to produce 1<em>H</em>-indazolo[1,2-b] phthalazine-1,6,11-triones and 1<em>H</em>-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives have been developed <em>via</em> multicomponent and one-pot reactions of various aldehydes, cyclic or acyclic 1,3-diketones with: <em>i)</em> phthalhydrazide or <em>ii)</em> phthalic anhydride-hydrazinium hydroxide using wet 2,4,6-trichlorotriazine (TCT) as catalyst under solvent-free conditions. Simple and mild reaction conditions, the use of a cheap catalyst and easy workup and isolation are notable features of this method.</p>


2013 ◽  
Vol 10 (10) ◽  
pp. 764-769 ◽  
Author(s):  
Akbar Mobinikhaledi ◽  
Alireza Amiri

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.


2010 ◽  
Vol 60 (3) ◽  
pp. 517-528 ◽  
Author(s):  
Marcio R Loos ◽  
Volker Abetz ◽  
Karl Schulte

2020 ◽  
Vol 56 (55) ◽  
pp. 7665-7668 ◽  
Author(s):  
Lu Liu ◽  
Lei Li ◽  
Shukuan Mao ◽  
Xin Wang ◽  
Ming-Dong Zhou ◽  
...  

Various o-alkenyl aromatic isocyanides were prepared from readily available reactants for their double annulation with diazo compounds for a one-pot synthesis of pyrazolo[1,5-c]quinazolines under mild reaction conditions.


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.


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