scholarly journals The Role Ionic Liquid [BMIM][PF6] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction

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
Keyword(s):  
Ionic Liquid ◽  
Yield Loss ◽  
Allyl Bromide ◽  
Reaction Times ◽  
Prins Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Barbier Reaction ◽  
Significant Yield

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.

Tributylhexadecylphosphonium bromide: an efficient reagent system for the one-pot synthesis of 2,4,5-trisubstituted imidazoles

2015 ◽  
Vol 21 (2) ◽  
Author(s):  
Mohammad Heidari ◽  
Mohsen Rezaei ◽  
Rashid Badri
Keyword(s):  
Cost Effectiveness ◽  
Aromatic Aldehyde ◽  
Ammonium Acetate ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Efficient Reagent

AbstractThe reaction of benzil, an aromatic aldehyde, and ammonium acetate in ethanol at reflux in the presence of tributylhexadecylphosphonium bromide as catalyst affords a 2,4,5-trisubstituted imidazole. The present methodology offers several advantages over the literature methods, including excellent yields, shorter reaction times, environmentally benign milder reaction conditions, cost-effectiveness of catalyst, easy workup, and purification of products by nonchromatographic methods.

CuO Nanoparticles: A Mild and Efficient Reusable Catalyst for the One-Pot Synthesis of 4-amino-5-pyrimidinecarbonitriles under Aqueous Conditions

2012 ◽  
Vol 326-328 ◽  
pp. 372-376
Author(s):  
Seyed Javad Ahmadi ◽  
Sodeh Sadjadi ◽  
Morteza Hosseinpour
Keyword(s):  
Efficient Method ◽  
Reaction Times ◽  
Cuo Nanoparticles ◽  
Reusable Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One ◽  
Aqueous Conditions

An efficient method for the synthesis of 4-amino-5-pyrimidinecarbonitriles by three-component reaction of malononitrile, aldehydes and N-unsubstituted amidines, under aqueous conditions, using CuO nanoparticles as catalyst is reported. The protocol offers advantages in terms of higher yields, short reaction times, and mild reaction conditions, with reusability of the catalyst.

scholarly journals Multi-component synthesis of piperidines and dihydropyrrol-2-one derivatives catalyzed by a dual-functional ionic liquid

2019 ◽  
Vol 44 (1-2) ◽  
pp. 20-24 ◽  
Author(s):  
Narjes Basirat ◽  
Seyed Sajad Sajadikhah ◽  
Abdolkarim Zare
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Reaction Conditions ◽  
One Pot ◽  
Dialkyl Acetylenedicarboxylates ◽  
Dual Functional

N,N,N’, N’-tetramethyl- N,N’-bis(sulfo)ethane-1,2-diaminium mesylate ([TMBSED][OMs]2) was employed for the synthesis of piperidines and dihydropyrrol-2-ones via one-pot multi-component reactions in simple and green processes. This pseudo five-component reaction of aromatic aldehydes, anilines and alkyl acetoacetates was carried out under reflux conditions in ethanol to afford substituted piperidines. Also, dihydropyrrol-2-one derivatives were synthesized by means of four-component reactions of various amines, dialkyl acetylenedicarboxylates and formaldehyde in ethanol at room temperature. The present approaches have several advantages such as good yields, easy work-ups, short reaction times, and utilize mild and clean reaction conditions.

scholarly journals Solvent-Free Green and Efficient One-Pot Synthesis of Dihydropyrano[3,2-c]chromene Derivatives

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Shubha Jain ◽  
Deepika Rajguru ◽  
Balwant S. Keshwal ◽  
Aman D. Acharya
Keyword(s):  
Efficient Method ◽  
Present Method ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Reaction Conditions ◽  
One Pot ◽  
Highly Efficient ◽  
One Pot Synthesis

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.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

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.

Synthesis of pyrazolo[1,5-c]quinazoline derivatives through the copper-catalyzed domino reaction of o-alkenyl aromatic isocyanides with diazo compounds

2020 ◽  
Vol 56 (55) ◽  
pp. 7665-7668 ◽  
Author(s):  
Lu Liu ◽  
Lei Li ◽  
Shukuan Mao ◽  
Xin Wang ◽  
Ming-Dong Zhou ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Quinazoline Derivatives

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.

scholarly journals One-Pot Synthesis of Novel Multisubstituted 1-Alkoxyindoles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1466
Author(s):  
Ye Eun Kim ◽  
Hyunsung Cho ◽  
Yoo Jin Lim ◽  
Chorong Kim ◽  
Sang Hyup Lee
Keyword(s):  
Alkyl Halide ◽  
The Novel ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Consecutive Reactions ◽  
Intramolecular Condensation ◽  
Synthetic Sequence ◽  
Novel Target

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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