Palladium-catalyzed one-pot cycloaddition reactions of thioureas with 3H-indol-3-ones generated in situ from 2-alkynyl arylazides: rapid and efficient access to imidazoloindolines

2020 ◽  
Vol 7 (21) ◽  
pp. 3480-3485
Author(s):  
Ping Li ◽  
Boyu Zhu ◽  
Yao Xu ◽  
Zhiqiang Zhou ◽  
Guiwen Hu ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Efficient Access ◽  
Palladium Catalyzed

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

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.

Palladium-Catalyzed One-Pot Synthesis of C2-Quaternary Indolin-3-ones via 1H -indole-3-sulfonates Generated in Situ from 2-Alkynyl Arylazides and Sulfonic Acids

2017 ◽  
Vol 359 (23) ◽  
pp. 4147-4152 ◽  
Author(s):  
Xiaoxiang Zhang ◽  
Ping Li ◽  
Chang Lyu ◽  
Wanxiong Yong ◽  
Jing Li ◽  
...  
Keyword(s):  
Sulfonic Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed

One-Pot Synthesis of 2-Substituted Benzoxazoles Directly from Carboxylic Acids

2008 ◽  
Vol 61 (11) ◽  
pp. 881 ◽  
Author(s):  
Dinesh Kumar ◽  
Santosh Rudrawar ◽  
Asit K. Chakraborti
Keyword(s):  
Carboxylic Acids ◽  
Methanesulfonic Acid ◽  
Acid Chlorides ◽  
Double Bonds ◽  
Reaction Conditions ◽  
One Pot ◽  
Effective Catalyst ◽  
One Pot Synthesis ◽  
Highly Effective

Methanesulfonic acid has been found to be a highly effective catalyst for a convenient and one-pot synthesis of 2-substituted benzoxazoles by the reaction of 2-aminophenol with acid chlorides, generated in situ from carboxylic acids. Aryl, heteroaryl, and arylalkyl carboxylic acids provided excellent yields of the corresponding benzoxazoles. The reaction conditions were compatible with various substituents such as chloro, bromo, nitro, methoxy, cyclopentyloxy, phenoxy, thiophenoxy, and conjugated double bonds. Benzoxazole formation was found to be general with respect to substituted 2-aminophenols.

2-Phenyl-2,3-dihydrobenzo[d]thiazole: A Mild, Efficient, and Highly Active in situ Generated Chemoselective Reducing Agent for the One-Pot Synthesis of 5-Monoalkylbarbiturates in Water

Synlett ◽  
2017 ◽  
Vol 29 (04) ◽  
pp. 477-482 ◽  
Author(s):  
Dibakar Deka ◽  
Subarna Kalita
Keyword(s):  
Reducing Agent ◽  
High Yield ◽  
Purification Process ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Highly Active ◽  
The One ◽  
Operational Simplicity

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.

scholarly journals One-Pot Synthesis of B-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1348
Author(s):  
Sergey A. Anufriev ◽  
Akim V. Shmal’ko ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev
Keyword(s):  
Functional Groups ◽  
X Ray Diffraction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions ◽  
The One ◽  
Solid State Structures ◽  
Derivatives Of

The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.

Synthesis of Internal Alkynes through an Effective Tandem ­Elimination–Hydrodebromination–Cross-Coupling of gem-­Dibromoalkenes with Halobenzenes

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 209-214 ◽  
Author(s):  
Yuan Ji ◽  
Ning Zhong ◽  
Zinan Kang ◽  
Guobing Yan ◽  
Ming Zhao
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Sonogashira Coupling Reaction ◽  
Palladium Catalyzed ◽  
Internal Alkyne

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

scholarly journals “In Situ” Generated “HCl”: A Highly Efficient Catalyst for One-Pot Synthesis of 1H-Indazolo [1,2-b]phthalazine-1,6,11-triones and 1Hpyrazolo[1,2-b]phthalazine-5,10-diones under Solvent-Free Conditions

2017 ◽  
Vol 58 (2) ◽  
Author(s):  
Behrooz Maleki ◽  
Samaneh Sedigh Ashrafi
Keyword(s):  
Phthalic Anhydride ◽  
Solvent Free ◽  
Synthetic Route ◽  
Reaction Conditions ◽  
One Pot ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
One Pot Synthesis ◽  
Solvent Free Conditions

<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>

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

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.

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.

Sign in / Sign up

Export Citation Format

Share Document