Metal-free Synthesis of N-Sulfonylformamidines via Skeletal Reconstruction of Sulfonyl Oximonitriles

2022 ◽  
Author(s):  
Feng Li ◽  
Ziyan Wu ◽  
Jingjing Wang ◽  
Siyuan Zhang ◽  
Jiaxin Yu ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Domino Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
High Yields ◽  
Skeletal Reconstruction

We firstly develop an unprecedented domino reaction of sulfonyl oximonitriles with secondary amines to streamline synthesis of N-sulfonylformamidines in decent to high yields under mild reaction conditions. In addition, the...

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

scholarly journals Design, Synthesis, and In Vitro Evaluation of Benzofuro[3,2-c]Quinoline Derivatives as Potential Antileukemia Agents

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 203 ◽  
Author(s):  
Ying Lin ◽  
Dong Xing ◽  
Wen-Biao Wu ◽  
Gao-Ya Xu ◽  
Li-Fang Yu ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Biological Evaluation ◽  
Quinoline Derivatives ◽  
Reaction Conditions ◽  
Design Synthesis ◽  
In Vitro Evaluation ◽  
Metal Free ◽  
Sequential Transformation ◽  
High Yields

Herein, we design and synthesize an array of benzofuro[3,2-c]quinolines starting from 3-(2-methoxyphenyl)quinolin-4(1H)ones via a sequential chlorination/demethylation, intramolecular cyclization pathway. This sequential transformation was efficient, conducted under metal-free and mild reaction conditions, and yielded corresponding benzofuro[3,2-c]quinolines in high yields. In vitro biological evaluation indicated that such type of compounds showed excellent antileukemia activity and selectivity, and therefore may offer a promising hit compound for developing antileukemia compounds.

scholarly journals Direct access to multi-functionalized benzenes via [4 + 2] annulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes

RSC Advances ◽  
2020 ◽  
Vol 10 (49) ◽  
pp. 29171-29174 ◽  
Author(s):  
Qianfa Jia ◽  
Yunfei Lan ◽  
Xin Ye ◽  
Yinhe Lin ◽  
Qiao Ren
Keyword(s):  
Direct Access ◽  
Reaction Conditions ◽  
Metal Free ◽  
Unsaturated Aldehydes ◽  
Wide Range ◽  
High Yields

An efficient [4 + 2] benzannulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes was achieved under metal-free reaction conditions selectively delivering a wide range of polyfunctional benzenes in high yields respectively (up to 94% yield).

One-pot and Three-Component Synthesis of α-Benzylamino Pyrones

2017 ◽  
Vol 41 (1) ◽  
pp. 42-44 ◽  
Author(s):  
Jilla Sanchooli ◽  
Alireza Hassanabadi
Keyword(s):  
Oxalic Acid ◽  
Aqueous Media ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Secondary Amines ◽  
Reaction Conditions ◽  
One Pot ◽  
Aerobic Conditions ◽  
Salient Features ◽  
High Yields

The synthesis of α-benzylamino pyrones is described involving the reaction of 4-hydroxy-6-methyl-2 H-pyran-2-one with aromatic aldehydes and secondary amines in the presence of oxalic acid and in aqueous media. The salient features of this protocol are aerobic conditions, short reaction times, milder reaction conditions without additives and high yields.

Transition-Metal-Free Synthesis of Trifluoromethylated Furans via a Bu3P-Mediated Tandem Acylation–Wittig Reaction

Synlett ◽  
2020 ◽  
Vol 31 (20) ◽  
pp. 2035-2038
Author(s):  
Wei Zhou ◽  
Maizhan Li
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Nucleophilic Addition ◽  
Wittig Reaction ◽  
Reaction Conditions ◽  
Metal Free ◽  
Highly Efficient ◽  
Intramolecular Wittig Reaction ◽  
High Yields

AbstractA highly efficient nucleophilic addition–O-acylation–intramolecular Wittig reaction of β-trifluoromethyl α,β-enones is disclosed. This strategy features mild reaction conditions and provides a practical transition-metal-free method to a set of biologically significant trifluoromethylated furans in high yields with diverse functional groups.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

scholarly journals Iodide/H2O2 Catalyzed Intramolecular Oxidative Amination for the Synthesis of 3,2′-Pyrrolidinyl Spirooxindoles

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2265 ◽  
Author(s):  
Yu-Ting Gao ◽  
Xiao-Yang Jin ◽  
Qi Liu ◽  
An-Di Liu ◽  
Liang Cheng ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Ammonium Iodide ◽  
Reaction Conditions ◽  
Oxidative Amination ◽  
Metal Free ◽  
High Yields

An ammonium iodide/hydrogen peroxide-mediated intramolecular oxidative amination of 3-aminoalkyl-2-oxindoles was achieved, affording the corresponding 3,2′-pyrrolidinyl spirooxindoles and their 6- or 7-membered analogous in moderate to high yields. This metal-free procedure features very mild reaction conditions, non-toxicity and easily handled hydrogen peroxide as a clean oxidant.

Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2076-2080 ◽  
Author(s):  
Wen-Ting Wei ◽  
Zhiyong Guo ◽  
Guodong Zhou ◽  
Xu-Dong Xu ◽  
Gan-Ping Chen
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Coupling Process ◽  
Metal Free ◽  
Radical Coupling ◽  
Radical Coupling Reaction ◽  
High Yields

An efficient and practical transition-metal-free radical ­coupling reaction of sulfonyl hydrazides mediated by NIS/K2S2O8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S–S bonds.

scholarly journals Metal-Free Synthesis of Biaryl- and Teraryl-Cored Diarylmethanes by Ring Transformation of 2H-Pyran-2-ones

Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1435-1444 ◽  
Author(s):  
Fateh Singh ◽  
Priyanka Kole
Keyword(s):  
Reaction Products ◽  
Ring Transformation ◽  
Reaction Conditions ◽  
Metal Free ◽  
High Yields

An efficient metal-free approach for the synthesis of functionalized biaryl-cored diarylmethanes is described by the ring transformation of 2H-pyran-2-ones using 4-phenylbutan-2-one as carbanion source. Moreover, 2H-pyran-2-ones were reacted with 1,3-diphenylacetone in the presence of base to achieve functionalized teraryl-cored diarylmethanes. All the ring transformation reactions were performed under mild reaction conditions to afford the biaryl- and teraryl-cored reaction products in high yields.

scholarly journals Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 410
Author(s):  
Emanuela Calcio Gaudino ◽  
Elisa Acciardo ◽  
Silvia Tabasso ◽  
Maela Manzoli ◽  
Giancarlo Cravotto ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Nitro Compounds ◽  
Secondary Amines ◽  
Cross Linking ◽  
Reaction Conditions ◽  
One Pot ◽  
Microwave Assisted ◽  
Aldehydes And Ketones ◽  
Bimetallic Nanocatalysts ◽  
High Yields

The optimization of sustainable protocols for reductive amination has been a lingering challenge in green synthesis. In this context, a comparative study of different metal-loaded cross-linked cyclodextrins (CDs) were examined for the microwave (MW)-assisted reductive amination of aldehydes and ketones using either H2 or formic acid as a hydrogen source. The Pd/Cu heterogeneous nanocatalyst based on Pd (II) and Cu (I) salts embedded in a β-CD network was the most efficient in terms of yield and selectivity attained. In addition, the polymeric cross-linking avoided metal leaching, thus enhancing the process sustainability; good yields were realized using benzylamine under H2. These interesting findings were then applied to the MW-assisted one-pot synthesis of secondary amines via a tandem reductive amination of benzaldehyde with nitroaromatics under H2 pressure. The formation of a CuxPdy alloy under reaction conditions was discerned, and a synergic effect due to the cooperation between Cu and Pd has been hypothesized. During the reaction, the system worked as a bifunctional nanocatalyst wherein the Pd sites facilitate the reduction of nitro compounds, while the Cu species promote the subsequent imine hydrogenation affording structurally diverse secondary amines with high yields.

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