Transition-metal-free synthesis of 5-amino-1,2,3-triazoles via nucleophilic addition/cyclization of carbodiimides with diazo compounds

2021 ◽  
Author(s):  
Shilong Wang ◽  
Yuanyuan Zhang ◽  
Guixin Liu ◽  
Hui Xu ◽  
Lijuan Song ◽  
...  
Keyword(s):  
Transition Metal ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
Diazo Compounds ◽  
Metal Free

A facile and transition-metal-free synthesis of functionalized 5-amino-1,2,3-triazoles with good functional-group tolerance and regioselectivity via nucleophilic addition/cyclization has been described.

Direct and metal-free oxidative amination of sp3 C–H bonds for the construction of 2-hetarylquinazolin-4(3H)-ones

2016 ◽  
Vol 3 (9) ◽  
pp. 1096-1099 ◽  
Author(s):  
Huanhuan Liu ◽  
Tianran Zhai ◽  
Shiteng Ding ◽  
Yalei Hou ◽  
Xiangyu Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
New Method ◽  
Oxidative Amination ◽  
Metal Free ◽  
Mild Conditions

New method for synthesis of 2-hetarylquinazolin-4(3H)-ones from 2-aminobenzamides and (2-azaaryl)methanes under transition-metal free conditions, featuring a wide substrate scope with a broad range of functional group tolerance under mild conditions.

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N-Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Yadong Sun ◽  
Ablimit Abdukader ◽  
Yuhan Lu ◽  
Chenjiang Liu
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Room Temperature ◽  
Functional Group ◽  
Ammonium Thiocyanate ◽  
Potassium Persulfate ◽  
Sulfur Source ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Metal Free

AbstractA highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance. This protocol can be scaled up to a gram level and can be applied to coupling reactions with 4-(4-bromophenyl)-1,2,3-thiadiazole as the substrate.

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Synthesis ◽  
2021 ◽  
Author(s):  
Yury N. Kotovshchikov ◽  
Stepan S. Tatevosyan ◽  
Gennadij V. Latyshev ◽  
Nikolay V. Lukashev ◽  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Cost Effective ◽  
Reductive Cleavage ◽  
Effective Procedure ◽  
Free Base ◽  
Metal Free ◽  
Fused Heterocycles ◽  
Convenient Approach

AbstractA convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

scholarly journals gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors

2015 ◽  
Vol 137 (45) ◽  
pp. 14496-14501 ◽  
Author(s):  
Mingyou Hu ◽  
Chuanfa Ni ◽  
Lingchun Li ◽  
Yongxin Han ◽  
Jinbo Hu
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Diazo Compounds ◽  
Metal Free

scholarly journals SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

RSC Advances ◽  
2020 ◽  
Vol 10 (29) ◽  
pp. 17288-17292 ◽  
Author(s):  
Yiyong Zhao ◽  
Junjie Wei ◽  
Shuting Ge ◽  
Guofu Zhang ◽  
Chengrong Ding
Keyword(s):  
Transition Metal ◽  
Nitrogen Source ◽  
Functional Group ◽  
Cascade Process ◽  
One Pot ◽  
Metal Free ◽  
Work Up

Our gram-scale process uses abundant and inexpensive aldehydes, a clean nitrogen source, requires no additional carbon atoms, is transition-metal free, and features easy work-up and excellent functional group compatibility.

Direct Propargylation of ortho-Quinone Methides with Alkynyl Zinc Reagents: An Application to the One-Pot Synthesis of 2,3-Disubstituted Benzofurans

Synlett ◽  
2020 ◽  
Vol 31 (08) ◽  
pp. 818-822
Author(s):  
Hongjun Ren ◽  
Manman Sun ◽  
Jinyu Song ◽  
Lei Wang ◽  
Wenguang Yin ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Quinone Methides ◽  
One Pot ◽  
Metal Free ◽  
Efficient Strategy ◽  
One Pot Synthesis ◽  
Subsequent Cyclization ◽  
The One

A transition-metal-free propargylation of ortho-quinone methides (o-QMs) with alkynyl zinc reagents was achieved. A conjugate alkynylation of an o-QM and subsequent cyclization sequence in the presence of KOt-Bu for the synthesis of 2,3-disubstituted benzofurans in one pot was developed. This efficient strategy exhibits good functional-group compatibility and gives moderate to good yields. The present reaction might serve as an attractive method for the synthesis of polysubstituted benzofurans.

Diastereoselective synthesis of spiro[cyclopropane-1,3′-indolin]-2′-ones through metal-free cyclopropanation using tosylhydrazone salts

RSC Advances ◽  
2014 ◽  
Vol 4 (72) ◽  
pp. 38425-38432 ◽  
Author(s):  
Jeevak Sopanrao Kapure ◽  
Chada Narsimha Reddy ◽  
Praveen Reddy Adiyala ◽  
Ranjita Nayak ◽  
V. Lakshma Nayak ◽  
...  
Keyword(s):  
Transition Metal ◽  
Diazo Compounds ◽  
Diastereoselective Synthesis ◽  
Metal Free

Anticancer spiro[cyclopropane-1,3′-indolin]-2′-ones are accessible through a transition metal-free diastereoselective cyclopropanation using in situ generated diazo-compounds.

Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution

2019 ◽  
Vol 55 (87) ◽  
pp. 13124-13127 ◽  
Author(s):  
Zhicheng Fu ◽  
Simin Sun ◽  
Anjian Yang ◽  
Fang Sun ◽  
Jiaxi Xu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Michael Addition ◽  
Nucleophilic Addition ◽  
Free Access ◽  
Metal Free

3,4-Dihydro-1,2-oxaphosphinine 2-oxides are synthesized through tandem intermolecular nucleophilic addition and cyclization of phosphonochloridates and enones in the presence of base.

Application of α-amino acids for the transition-metal-free synthesis of pyrrolo[1,2-a]quinoxalines

2017 ◽  
Vol 15 (34) ◽  
pp. 7157-7164 ◽  
Author(s):  
Huanhuan Liu ◽  
Feiyu Zhou ◽  
Wen Luo ◽  
Yuxin Chen ◽  
Chenyang Zhang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Transition Metal ◽  
Functional Group ◽  
Efficient Synthesis ◽  
Metal Free

A practical and concise protocol for the efficient synthesis of pyrrolo[1,2-a]quinoxalines from readily available α-amino acids and 2-(1H-pyrrol-1-yl)anilines under transition metal-free conditions has been established. This protocol, which includes the formation of new C–C and C–N bonds, features a wide substrate scope with a broad range of functional group tolerance.

Visible-light-promoted selective C–H amination of heteroarenes with heteroaromatic amines under metal-free conditions

2017 ◽  
Vol 15 (45) ◽  
pp. 9590-9594 ◽  
Author(s):  
Supravat Samanta ◽  
Chitrakar Ravi ◽  
Sadu Nageswara Rao ◽  
Abhisek Joshi ◽  
Subbarayappa Adimurthy
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Metal Free ◽  
High Degree

The regioselective C–H amination of quinoline amides (C5) and imidazopyridines (C3) under transition-metal-free conditions at room temperature with a high degree of functional group tolerance is reported.

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