Recent Developments in N2-Selective Functionalizations of 1,2,3-Triazoles

The widespread use of 1,2,3-triazole compounds in drugs has resulted in a great interest in the efficient synthesis of N2-substituted 1,2,3-triazoles via post triazole functionalization methods. At present, there are many methods for the synthesis of N1-substituted 1,2,3-triazole compounds, but the development of convenient methods for the N2-selective functionalization of 1,2,3-triazoles remains challenging. In general, the greater stability of the N1 tautomer makes the N2 position a non-preferable reactive site, which has limited the application of 1,2,3-triazoles. In this review, we summarized advances in the direct N2-selective functionalization of 1,2,3-triazoles since 2008.1 Introduction2 N2-Alkylation3 N2-Allylation4 N2-Propargylation5 N2-Alkenylation6 N2-Alkynylation7 N2-Arylation8 Conclusions and Outlook

[1]  Pengfei Li,et al.  Organocatalytic Regio- and Enantioselective 1,8-Additions of Nitrogen and Sulfur Nucleophiles to 6-Methylene-6H-indoles. , 2020, Organic letters.

[2]  S. Akai,et al.  Cobalt-Catalyzed Intermolecular Markovnikov Hydroamination of Nonactivated Olefins: N2-Selective Alkylation of Benzotriazole. , 2020, Organic letters.

[3]  Trevor A. Hamlin,et al.  Ligand‐Mediated Regioselective Rhodium‐Catalyzed Benzotriazole–Allene Coupling: Mechanistic Exploration and Quantum Chemical Analysis , 2019, Chemistry.

[4]  S. C. Suri,et al.  Catalyst-Free Regioselective N2 Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts. , 2019, Organic letters.

[5]  F. Xia,et al.  Highly Regioselective Radical Transformation of N-Sulfonyl-1,2,3-triazoles in Air. , 2019, Organic letters.

[6]  I. Beletskaya,et al.  Copper(I)‐Catalyzed Regioselective Chan‐Lam N 2‐Vinylation of 1,2,3‐Triazoles and Tetrazoles , 2019, Advanced Synthesis & Catalysis.

[7]  Xinhao Zhang,et al.  Rhodium-Catalyzed Regioselective N2 -Alkylation of Benzotriazoles with Diazo Compounds/Enynones via a Nonclassical Pathway. , 2018, Angewandte Chemie.

[8]  R. Peddinti,et al.  Asymmetric Organocatalytic Approach to 2,4-Disubstituted 1,2,3-Triazoles by N2-Selective Aza-Michael Addition. , 2018, The Journal of organic chemistry.

[9]  Y. Nelyubina,et al.  Synthesis and Regioselective N‐2 Functionalization of 4‐Fluoro‐5‐aryl‐1,2,3‐NH‐triazoles , 2017 .

[10]  Virender Singh,et al.  Medicinal attributes of 1,2,3-triazoles: Current developments. , 2017, Bioorganic chemistry.

[11]  J. Bourguignon,et al.  Functionalization of 2H-1,2,3-Triazole C-Nucleoside Template via N(2) Selective Arylation. , 2016, The Journal of organic chemistry.

[12]  Zili Chen,et al.  N(2)-Selective Iodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N(2)-Alkyl-Substituted 1,2,3-Triazoles. , 2016, The Journal of organic chemistry.

[13]  M. Shi,et al.  Lewis Acid Catalyzed Intramolecular Ring-Opening of Triazole-Substituted Methylenecyclopropanes: An Approach to 4H-[1,2,3]Triazolopyrazines and 4H-[1,2,3]Triazolo[1,4]diazepines , 2014, Synlett.

[14]  B. Breit,et al.  Unlocking the N(2)  selectivity of benzotriazoles: regiodivergent and highly selective coupling of benzotriazoles with allenes. , 2014, Angewandte Chemie.

[15]  Zhen Wang,et al.  Highly N2-selective coupling of 1,2,3-triazoles with indole and pyrrole. , 2014, Chemistry.

[16]  Z. Yao,et al.  Synthesis of 2-vinyl-2H-benzotriazoles via NIS-promoted regio/stereoselective addition of 1H-benzotriazole to alkynes , 2013 .

[17]  Xiaodong Shi,et al.  Synthesis of allene triazole through iron catalyzed regioselective addition to propargyl alcohols. , 2012, Chemical communications.

[18]  S. Buchwald,et al.  Me3(OMe)tBuXPhos: a surrogate ligand for Me4tBuXPhos in palladium-catalyzed C-N and C-O bond-forming reactions. , 2012, The Journal of organic chemistry.

[19]  Xiaodong Shi,et al.  Mitsunobu reaction of 1,2,3-NH-triazoles: a regio- and stereoselective approach to functionalized triazole derivatives. , 2011, Chemistry, an Asian journal.

[20]  S. Buchwald,et al.  Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles. , 2011, Angewandte Chemie.

[21]  T. Kitamura,et al.  Alkynylation of benzotriazole with silylethynyliodonium triflates. Regioselective synthesis of 2-ethynyl-2H-benzotriazole derivatives. , 2011, The Journal of organic chemistry.

[22]  P. Wipf,et al.  General solution to the synthesis of N-2-substituted 1,2,3-triazoles. , 2010, Organic letters.

[23]  C. Senanayake,et al.  Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles. , 2009, Organic letters.

[24]  C. Senanayake,et al.  Highly regioselective N-2 arylation of 4,5-dibromo-1,2,3-triazole: efficient synthesis of 2-aryltriazoles. , 2009, Organic letters.

[25]  Jihui Li,et al.  Facile one-pot synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles through Sonogashira coupling/1,3-dipolar cycloaddition of acid chlorides, terminal acetylenes, and sodium azide. , 2009, Organic letters.

[26]  Xiaodong Shi,et al.  Highly efficient synthesis of vinyl substituted triazoles by Au(I) catalyzed alkyne activation. , 2009, Bioorganic & medicinal chemistry letters.

[27]  Yuxiu Liu,et al.  Efficient synthesis of N-2-aryl-1,2,3-triazole fluorophores via post-triazole arylation. , 2008, Organic letters.

[28]  Yuxiu Liu,et al.  Conformational control in the regioselective synthesis of N-2-substituted-1,2,3-triazoles. , 2008, Chemical communications.

[29]  K. Sharpless,et al.  Efficient synthesis of 2-substituted-1,2,3-triazoles. , 2008, Organic letters.