scholarly journals One-Pot Synthesis of Heavier Group 14 N-Heterocyclic Carbene Using Organosilicon Reductant

Inorganics ◽  
2018 ◽  
Vol 6 (3) ◽  
pp. 69 ◽  
Author(s):  
Ravindra Raut ◽  
Sheikh Amin ◽  
Padmini Sahoo ◽  
Vikas Kumar ◽  
Moumita Majumdar

Syntheses of heavier Group 14 analogues of “Arduengo-type” N-heterocyclic carbene majorly involved the use of conventional alkali metal-based reducing agents under harsh reaction conditions. The accompanied reductant-derived metal salts and chances of over-reduced impurities often led to isolation difficulties in this multi-step process. In order to overcome these shortcomings, we have used 1,4-bis-(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene as a milder reducing agent for the preparation of N-heterocyclic germylenes (NHGe) and stannylenes (NHSn). The reaction occurs in a single step with moderate yields from the mixture of N-substituted 1,4-diaza-1,3-butadiene, E(II) (E(II) = GeCl2·dioxane, SnCl2) and the organosilicon reductant. The volatile byproducts trimethylsilyl chloride and pyrazine could be removed readily under vacuum. No significant over reduction was observed in this process. However, N-heterocyclic silylene (NHSi) could not be synthesized using an even stronger organosilicon reductant under thermal and photochemical conditions.

2013 ◽  
Vol 571 ◽  
pp. 169-196
Author(s):  
Nigamananda Das

Methyl isobutyl ketone (MIBK) is one of the most widely produced and used aliphatic ketones worldwide. The one-step MIBK process with no intermediate separation steps using multifunctional catalysts is an important development towards greener organic synthesis and generates tremendous interest among the researcher across the globe. The single step process is facile and more economically viable and has provided opportunity to develop new and improved catalyst systems capable of operating under mild conditions. A widely variety of catalytic systems have been used in one-step process during last three to four decades. The progress in one-pot synthesis of MIBK using different multifunctional catalysts with special reference to layered based catalysts was critically reviewed in this article.


Synlett ◽  
2017 ◽  
Vol 29 (04) ◽  
pp. 477-482 ◽  
Author(s):  
Dibakar Deka ◽  
Subarna Kalita

A metal- and catalyst-free reductive alkylation protocol for the one-pot synthesis of 5-monoalkylbarbiturates from barbituric acids and aldehydes using the in situ generated chemoselective reducing agent 2-phenyl-2,3-dihydrobenzo[d]thiazole from 2-aminothiophenol and benzaldehyde is described. The notable advantages of the protocol are operational simplicity, mild reaction conditions, high yield, short reaction time, and simple workup and purification process which make it highly attractive.


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.


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.


2020 ◽  
Vol 7 (21) ◽  
pp. 3480-3485
Author(s):  
Ping Li ◽  
Boyu Zhu ◽  
Yao Xu ◽  
Zhiqiang Zhou ◽  
Guiwen Hu ◽  
...  

An efficient palladium-catalyzed one-pot synthesis of imidazoloindolines from 2-alkynyl arylazides under mild reaction conditions has been described.


Molecules ◽  
2019 ◽  
Vol 24 (11) ◽  
pp. 2084
Author(s):  
Poliane K. Batista ◽  
João Marcos G. de O. Ferreira ◽  
Fabio P. L. Silva ◽  
Mario L. A. A Vasconcellos ◽  
Juliana A. Vale

Tetrahydropyran (THP) rings are common in several natural products, therefore, various strategies are being developed to synthesize these rings. The present work described the study of a one-pot synthesis of 2,4,6-trisubstituted tetrahydropyran compounds promoted by the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate [BMIM][PF6] through a Barbier–Prins reaction between allyl bromide and aldehydes. The use of [BMIM][PF6] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF6-, accelerates the Barbier reaction when used alone, and the excess SnBr2 from the reaction conditions of the Barbier reaction leads to the formation of the THP rings, thus acting as a catalyst for Prins cyclization. Additionally, we demonstrate that ionic liquid can be recovered and reused five times in the preparation of 4-bromo-tetrahydro-2,6-diphenyl-2H-pyran without significant yield loss.


RSC Advances ◽  
2016 ◽  
Vol 6 (100) ◽  
pp. 97629-97635 ◽  
Author(s):  
Hani Nasser Abdelhamid ◽  
Sekar Kumaran ◽  
Hui-Fen Wu

One-pot synthesis of cuprous ferrite (CuFeO2) nanoparticles modified with glycerol (glycerol@CuFeO2 NPs) using oligol and reducing agent was reported.


Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 668-672 ◽  
Author(s):  
Jianbo Zhang ◽  
Guosheng Sun ◽  
Yue Wu ◽  
Anqi Liu ◽  
Saifeng Qiu ◽  
...  

Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective, affordable, and green glycosylation procedure.


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