(3+2)-Cycloaddition of Donor–Acceptor Cyclopropanes with Thiocyanate: A Facile and Efficient Synthesis of 2-Amino-4,5-dihydrothiophenes

Synlett ◽  
2021 ◽  
Author(s):  
Daniel B. Werz ◽  
Anu Jacob ◽  
Philip Barkawitz ◽  
Ivan A. Andreev ◽  
Nina K. Ratmanova ◽  
...  
Keyword(s):  
Functional Groups ◽  
Ammonium Thiocyanate ◽  
Efficient Synthesis ◽  
Donor Acceptor ◽  
Efficient Route

AbstractAn easy and efficient route to obtain 2-amino-4,5-dihydrothiophenes is presented. A formal (3+2)-cycloaddition of donor–acceptor cyclopropanes and ammonium thiocyanate catalyzed by Yb(OTf)3 delivers the desired products in good to excellent yields. A broad range of functional groups is tolerated during this process.

Efficient Synthesis of O-Linked Glycoconjugates of Amino Acids from Carbohydrate-Derived Donor-Acceptor Cyclopropanes

Heterocycles ◽  
2019 ◽  
Vol 99 (1) ◽  
pp. 200
Author(s):  
Srinivasan Chandrasekaran ◽  
Gade Kishore ◽  
Vibha Gautam ◽  
Shrutisagar Dattatraya Haveli
Keyword(s):  
Amino Acids ◽  
Efficient Synthesis ◽  
Donor Acceptor

Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel–Crafts Reactions of Donor–Acceptor Aziridines with N,N-Dialkylanilines

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 281-289
Author(s):  
Yerin Kim ◽  
Yong Il Kwon ◽  
Sung-Gon Kim
Keyword(s):  
Lewis Acid ◽  
Efficient Synthesis ◽  
Broad Scope ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
High Yields

A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel–Crafts reaction of donor­–acceptor aziridines with N,N-dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88%), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich arenes, including dimethoxybenzene.

Efficient Synthesis of 3,4-Disubstituted 7-Azaindoles Employing SEM as a Dual Protecting–Activating Group

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2273-2278 ◽  
Author(s):  
Piroska Gyárfás ◽  
János Gerencsér ◽  
Warren S. Wade ◽  
László Ürögdi ◽  
Zoltán Novák ◽  
...  
Keyword(s):  
Functional Groups ◽  
Efficient Method ◽  
Reaction Times ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Efficient Synthesis ◽  
Mild Conditions

An efficient method for nucleophilic aromatic substitution on 7-azaindoles has been developed. The reaction is facilitated by the unique dual influence of SEM as both protecting and activating group, permitting mild conditions and short reaction times that are compatible with sensitive functional groups. The method is suitable for the synthesis of a broad range of products, most notably ethers.

Frontispiece: Stereoelectronic Chameleons: The Donor-Acceptor Dichotomy of Functional Groups

2017 ◽  
Vol 23 (14) ◽  
Author(s):  
Sergey Z. Vatsadze ◽  
Yulia D. Loginova ◽  
Gabriel dos Passos Gomes ◽  
Igor V. Alabugin
Keyword(s):  
Functional Groups ◽  
Donor Acceptor

Bis-ammonium immobilized polystyrenes with co-catalyzing functional end groups as efficient and reusable heterogeneous catalysts for synthesis of cyclic carbonate from CO2 and epoxides

RSC Advances ◽  
2016 ◽  
Vol 6 (3) ◽  
pp. 2217-2224 ◽  
Author(s):  
Qingyuan Deng ◽  
Gaohong He ◽  
Yu Pan ◽  
Xuehua Ruan ◽  
Wenji Zheng ◽  
...  
Keyword(s):  
Functional Groups ◽  
Heterogeneous Catalysts ◽  
Cyclic Carbonate ◽  
Efficient Synthesis ◽  
End Groups

Novel bis-ammonium immobilized polystyrenes with co-catalyzing functional groups were prepared for efficient synthesis of cyclic carbonate from CO2 and epoxides.

CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2191-2199 ◽  
Author(s):  
Yongde Zhao ◽  
Shengqiang Guo ◽  
Yang Zhou ◽  
Bencai Dai ◽  
Cuimeng Huo ◽  
...  
Keyword(s):  
Catalytic System ◽  
Sodium Azide ◽  
Room Temperature ◽  
Green Solvent ◽  
Efficient Synthesis ◽  
One Pot ◽  
Highly Efficient ◽  
Three Component Reaction ◽  
Efficient Route ◽  
Terminal Acetylenes

A concise one-pot three-component reaction of organic halides­, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.

scholarly journals Efficient Synthesis of α-Branched Purine-Based Acyclic Nucleosides: Scopes and Limitations of the Method

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4307
Author(s):  
Jan Frydrych ◽  
Lenka Poštová Slavětínská ◽  
Martin Dračínský ◽  
Zlatko Janeba
Keyword(s):  
Acetic Anhydride ◽  
Room Temperature ◽  
Side Chain ◽  
Efficient Synthesis ◽  
Purine Derivatives ◽  
Aliphatic Side Chain ◽  
Acyclic Nucleosides ◽  
Efficient Route ◽  
High Yields ◽  
Trimethylsilyl Trifluoromethanesulfonate

An efficient route to acylated acyclic nucleosides containing a branched hemiaminal ether moiety is reported via three-component alkylation of N-heterocycle (purine nucleobase) with acetal (cyclic or acyclic, variously branched) and anhydride (preferentially acetic anhydride). The procedure employs cheap and easily available acetals, acetic anhydride, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The multi-component reaction is carried out in acetonitrile at room temperature for 15 min and provides moderate to high yields (up to 88%) of diverse acyclonucleosides branched at the aliphatic side chain. The procedure exhibits a broad substrate scope of N-heterocycles and acetals, and, in the case of purine derivatives, also excellent regioselectivity, giving almost exclusively N-9 isomers.

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