Transition‐Metal‐Free Annulation of Sulfonyl‐Derived 1,3‐Enynes: Simple and Efficient Construction of 2,4‐Disubstituted Thiophenes and Vinyl Sulfone‐Tethered 1,2,3‐NH‐Triazoles
Wiley Online Library » Asian Journal of Organic Chemistry
by Sharadha Nunavath, Haritha Kumari Arram, Raju Jannapu Reddy
2d ago
Thiophenes and 1,2,3-NH-triazoles are important frameworks in pharmaceuticals and advanced functional materials. Vinyl sulfones are also blueprint motifs in medicinal chemistry, but hybrid analogues of 1,2,3-NH-triazole-derived from vinyl sulfones still need to be explored. In this report, we present an efficient and transition-metal-free [4+1]-thioannulation of sulfonyl-tethered 1,3-enynes with Na2S in the presence of Cs2CO3 to generate 2,4-disubstituted thiophenes in good to high yields. We also established a formal [3+2]-cycloaddition of 1,3-sulfonylenynes with NaN3 under metal- and base-fr ..read more
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Fe SAC on Nitrogen‐Doped Carbon: An Efficient Catalyst for S‐Alkylation of Dithiocarbamates via Borrowing Hydrogen Strategy
Wiley Online Library » Asian Journal of Organic Chemistry
by Vageesh M., Hima P., Preeti A. Bhobe, Raju Dey
3d ago
Fe single atom on nitrogen doped carbon as efficient, bench stable and recyclable catalyst for S-benzyl/alkylation of dithiocarbamates via borrowing hydrogen strategy. A wide range of functional groups are well tolerated and gave the desired dithiocarbamate products in good to excellent yields. Abstract Herein we report, the synthesis of single-atom iron on nitrogen-doped carbon as a catalyst for the direct formation of Csp3−S bond via borrowing hydrogen strategy using alcohols as the alkylating agent. The catalyst was synthesized by encapsulating ferrocene within the ZIF-8 framework, follow ..read more
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Synthesis of 1‐amino‐3‐aryl Naphthalenes from Bis(perfluoroalkanesulfonyl)imide with 1,2‐diethynylbenzenes
Wiley Online Library » Asian Journal of Organic Chemistry
by Takuji Kawamoto, Tetsushi Yamasaki, Tsubasa Ikazaki, Hiroshi Matsubara, Akio Kamimura
3d ago
Although the synthesis of vinyl triflates has a long history, the synthesis of vinyl bis(perfluoroalkanesulfonyl)imides has not been reported yet. Here, we report a simple synthetic route to vinyl bis(perfluoroalkanesulfonyl)imides that does not require any additives. The stereoselectivity originates from the steric hindrance between the aryl group and the imide. The reaction proceeds chemoselectively, and subsequent cyclization provides the 1-amino-3-aryl naphthalene dewrivatives. Abstract Although the synthesis of vinyl triflates has a long history, the synthesis of vinyl bis(perfluoroalka ..read more
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Metal‐Catalyzed Oxidative C−H Bond Functionalization of 1,4‐Benzoxazinones
Wiley Online Library » Asian Journal of Organic Chemistry
by Shankar Kumar, Rangnath Ravi, Tanu Sahu, Vikesh Kumar Jha, Renu Baweja, Abadh Kishor Jha
3d ago
This review covers Metal-Catalyzed Oxidative C(sp3)-H/C(sp2)-H Bond Functionalization Reactions on 1,4-Benzoxazinones with different coupling partners like indoles, phosphite, phosphine oxides, malonate esters and resorcinol. The synthesized products have shown their application in natural products, materials, agriculture and medicinal chemistry. Abstract The present review shows metal-catalyzed oxidative C(sp3)-H/C(sp2)-H bond functionalization of 1,4-benzoxazinones by utilizing various substrates such as indoles, phosphites or phosphine oxides, malonate esters, and resorcinol, which lead t ..read more
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Reaction Paradigms that Leverage Cycloaddition and Ring Strain to Construction Bicyclic Aryl Bioisosteres from Bicyclo[1.1.0]butanes
Wiley Online Library » Asian Journal of Organic Chemistry
by Stephen J. Sujansky, Xiaoshen Ma
3d ago
In this minireview, we discuss different cycloaddition methods to access strained C(sp 3)-rich bicyclic hydrocarbons, which are promising bioisosteres of aromatic rings. Each cycloaddition example is organized by four reaction paradigms, carbene cycloadditions, energy transfer promoted cycloadditions, electron transfer promoted cycloadditions, and cycloadditions occurring through polar pathways. A common theme we observed is strain energy and, where possible, we discuss its involvement. Abstract Within a medicinal chemist's toolbox, one of the most effective strategies to improve the overall ..read more
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An Emerging Strategy towards the Iodine‐Catalyzed Synthesis of Streptindole and its Derivatives in Water Medium
Wiley Online Library » Asian Journal of Organic Chemistry
by Parul Saini, Abhishek Nair, Anil J. Elias
3d ago
This study introduces a new metal-free method using iodine (I2) as a catalyst in aqueous conditions for synthesizing Streptindole and its derivatives. The approach is economically viable, easily handled, and exhibits remarkable tolerance to various functional groups. The protocol‘s versatility is showcased through the one-step total syntheses of alkaloid natural products Streptindole and Arsindoline B from indole. Abstract In this study, we propose an alternative metal-free methodology for the synthesis of Streptindole and its derivatives. This approach employs economically viable and easily ..read more
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Novel Isoxazolylpyrimidine Derivatives: Design, Synthesis, Antifungal Activity and In‐Silico Studies
Wiley Online Library » Asian Journal of Organic Chemistry
by Hari Krishnapura Nagaraja rao, Boja Poojary, Kavya Kallahalli Mohan Kumar, Govindan Chandrasehar, Krishnaveni Sannathammegowda, Anup Pandith
3d ago
A novel new class of Isoxazolylpyrimidine derivatives was synthesized efficiently with high purity (>95% by HPLC) under mild conditions. These compounds exhibited promising antifungal activity against diverse pathogenic fungal strains. In-depth in-silico studies using DFT, molecular docking, and molecular dynamics techniques revealed a plausible mechanism of action, these derivatives provide a new avenue towards future antifungal agents for crop protection. Abstract The advancement of environmentally friendly chemical synthesis in both academic and corporate research has recently taken on ..read more
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Copper‐Promoted Oxidative Amide‐Assisted Radical Selenylation of Anilides and N‐Arylsulfonamides with Diselenides
Wiley Online Library » Asian Journal of Organic Chemistry
by Lou Shi, Penghui Xu, Yingchun Ma, Yongrui Dong, Yanni Li, Deqiang Liang
3d ago
With the promotion of copper salts, a direct selenylation of N-arylsulfonamides and anilides has been developed. Depending on the substituents on the aniline rings, this approach can selectively achieve ortho-, para-, or unprecedented ortho, para-diselenylation of the aniline rings, and the resulting products can be separated by column chromatography. Mechanistic studies show the involvement of an amide-assisted radical strategy. Abstract A direct selenylation of N-arylsulfonamides and anilides using environmentally friendly and readily available copper promoted assisted by amide is presente ..read more
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Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction
Wiley Online Library » Asian Journal of Organic Chemistry
by Anna D. Zinoveva, Tatiana N. Borisova, Valeria A. Podchufarova, Anton P. Novikov, Anna A. Romanycheva, Anton A. Shetnev, Alexander A. Titov, Alexey V. Varlamov, Leonid G. Voskressensky
3d ago
A series of novel dipyrrolobenzo[1,2-a : 2′,1′-c][1,4]diazepine derivatives has been prepared using domino-reactions of pyrrolo[1,2-a][1,4]benzodiazepines with electron-deficient alkenes and via three component reaction between 2-(1-pyrrolyl)benzylamine, arylglyoxal monohydrate and alkenes. Multicomponent approach has been applied in the synthesis of indolizino[8,7-b]indole derivatives from tryptamine. The developed methods are simple and convenient procedures giving medium and excellent yields, showing a wide functional group tolerance. Abstract A three component reaction employing readily ..read more
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Enantioselective Vinylogous Mukaiyama‐Michael Reaction of Silyl Ketene Acetals to α,β‐Unsaturated 2‐Acyl Imidazoles to Construct 1,7‐dioxo Compounds
Wiley Online Library » Asian Journal of Organic Chemistry
by Mamta Gill, Arko Das, Vinod K. Singh
3d ago
We disclose Sc(III)-pybox catalyzed enantioselective vinylogous Mukaiyama-Michael reaction (VMMcR) of vinyl ketene silyl acetals with α,β-unsaturated 2-acyl imidazoles to construct enantioenriched 1,7-dioxo compounds. This is the first example of a metal-catalyzed asymmetric vinylogous Mukaiyama-Michael reaction using acyclic vinyl ketene acetals. This innovative approach to the formation of chiral 1,7-dioxo compounds illustrates excellent regio-, and enantioselectivities, demonstrating a broad substrate scope. Abstract The synthesis of chiral 1,7-dioxo compounds via Sc(III)-pybox catalyzed ..read more
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