Morpholine-mediated defluorinative cycloaddition of gem-difluoroalkenes and organic azides

• Tzu-Yu Huang,
• Mario Djugovski,
• Sweta Adhikari,
• Destinee L. Manning and
• Sudeshna Roy

Beilstein J. Org. Chem. 2023, 19, 1545–1554, doi:10.3762/bjoc.19.111

• ][12], inflammation [13], bacterial [14][15], and viral infections [16]. Hence, new ways to rapidly and efficiently access 1,2,3-triazole heterocyclic motifs are still in demand. However, methods for the direct synthesis of 1,4,5-trisubstituted-1,2,3-triazoles are limited [17]. This is highly desirable

• since the selective introduction of substituents at three different positions on the 1,2,3-triazole ring can augment the features of the molecule. Triazoles are also found in many biologically important molecules and functionalized materials [11][12][13][14][15][16]. 1,4,5-Trisubstituted-1,2,3-triazoles

• -promoted [22] azide–alkyne cycloaddition reactions [17][23][24]; however, most of these strategies use high temperatures [21][25]. Herein, we report the discovery of a novel, one-step regioselective method under mild conditions to obtain 1,4,5-trisubstituted-1,2,3-triazoles from gem-difluoroalkenes

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• industry. The current review aims to cover a wide literature survey of numerous synthetic strategies. Recent reports (2017–2021) in the field of 1,4,5-trisubstituted 1,2,3-triazoles are emphasized in this current review. Keywords: azides; Click reaction; [3 + 2]‐cycloaddition; fully functionalized 1,2,3

• -triazoles; N-containing heterocycles; 1,4,5-trisubstituted 1,2,3-triazoles; Introduction A high number of N-heterocycles [1][2][3][4] are identified, and this number is increasing very quickly [5][6][7][8]. Among them, the small heterocyclic ring of the 1,2,3-triazole is present in a broad variety of

• preparation of 1,4,5-trisubstituted 1,2,3-triazoles have gained much attention in triazole chemistry. Generally, two protocols for the synthesis of this type of triazole derivatives could be mentioned (metal or metal-free catalysis). Contrary to sporadic attempts [34], there is no detailed, systematic, and

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

• Mizuki Yamada,
• Mio Matsumura,
• Yuki Uchida,
• Masatoshi Kawahata,
• Yuki Murata,
• Naoki Kakusawa,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2016, 12, 1309–1313, doi:10.3762/bjoc.12.123

• ][10][11][12][13][14][15][16][17][18][19][20]. But the use of internal alkynes in CuAACs for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles is a more challenging area because of the difficulty in regiocontrol based on the increased steric hindrance [21][22]. A regioselective CuAAC synthesis of

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• , exchange of the halide group when 1-bromoalkynes are reacted with azides in the presence of copper(I) iodide [155] as observed by Rutjes et al. cannot be explained by this pathway. In 2006, the group of Nolan presented the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by cycloaddition reactions between

• release the triazole product. Excursus: copper-catalyzed cycloaddition reactions of 1-haloalkynes and internal alkynes Mononuclear mechanistic proposals are also worth mentioning in the context of cycloaddition reactions of haloalkynes and internal alkynes with organoazides to give 1,4,5-trisubstituted

• 1,2,3-triazoles. In 2005, the group of Rutjes reported the synthesis of 5-bromo-1,4-disubstituted-1,2,3-triazoles starting from 1-bromoalkynes [155]. In their optimized procedure, the bromoalkyne reacts with an azide in the presence of 5 mol % copper(I) iodide and 5 mol % copper(II) acetate in THF at 50

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• cases; Table 1, entries 3 and 4). 1,4,5-Trisubstituted 1,2,3-triazoles are of notable importance in drug discovery. For example, several 1,2,3-triazole-4,5-dicarboxylates display significant antituberculotic activity in vitro [69]. Thus, a nonterminal alkyne, diethyl acetylenedicarboxylate, was