How to cite this paper
Pokhodylo, N., Savka, R & Obushak, M. (2021). Comparison of synthetic routes for fully substituted (1H-1,2,3-triazol-4-yl)acetic acids.Current Chemistry Letters, 10(2), 53-66.
Refrences
1 Farooq T. (2020) Advances in Triazole Chemistry 1st Ed, Elsevier.
2 Pokhodylo N. T., Shyyka O. Ya, Goreshnik E. A., and Obushak M. D. (2020) 4-Phosphonated or 4-free 1,2,3-Triazoles: What controls the Dimroth reaction of arylazides with 2-oxopropylphosphonates? ChemistrySelect, 5 (1) 260–264.
3 Pokhodylo N. T., Shyyka O. Y. Savka, R. D., and Obushak, M. D. (2018) 2-Azido-1,3,4-thiadiazoles, 2-azido-1,3-thiazoles, and aryl azides in the synthesis of 1,2,3-triazole-4-carboxylic acids and their derivatives. Russ. J. Org. Chem. 54 (7) 1090–1099.
4 Pokhodylo N.T., and Matiychuk V. S. (2010) Synthesis of new 1,2,3-triazolo[1,5-a]quinazolinones. J. Heterocyclic Chem. 47 (2) 415–420.
5 Pokhodylo N.T., Matiychuk V.S., and Obushak M.D. (2009) Synthesis of the 1H-1,2,3-triazole derivatives by the cyclization of arylazides with 1-(1,3-benzothiazol-2-yl)acetone, 1,3-benzothiazol-2-ylacetonitrile and (4-aryl-1,3-thiazol-2-yl)acetonitrile. Chem. Heterocycl. Compd. 45 (4) 483–488.
6 Pokhodylo N.T., Matiychuk V.S., and Obushak M.D. (2009) Synthesis of Triazoles via Regioselective Reactions of Aryl Azides with Cyanoacetyl Pyrroles and Indoles. Synthesis (8) 1297–1300.
7 Jasiński R. (2015) Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study. Monatsh Chem 146 591–599.
8 Holla B. S., Mahalinga M., Karthikeyan M. S., Poojary B., Akberali P. M., and Kumari N. S. (2005) Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles. Eur. J. Med. Chem. 40 (11) 1173–1178.
9 Keillor J. W., Lubell W., and Pardin C. (2008) Cinnamoyl inhibitors of transglutaminase. WO 2008/144933.
10 Dong H.-S., Wang H.-C., Gao Z.-L., Li R.-S., and Cui F.-H. (2010) Tandem Michael addition/imino‐nitrile cyclization synthesis of 2‐amino‐6‐(1‐aryl‐5‐methyl‐1H‐1,2,3‐triazol‐4-yl)‐4‐phenylpyridine‐3‐carbonitrile. J. Heterocycl. Chem. 47 (2) 389–395.
11 Dong H.-S., Wang Y.-F., Shen G.-L., Dong W.-J., and Quan B. (2012) Synthesis of some new 1‐acyl‐5‐aryl‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐4,5‐dihydro‐1H‐pyrazole. J. Heterocycl. Chem. 49 (1) 149–152.
12 Abdel-Wahab B. F., Mohamed H. A., Abdel-Latif E., and Awad G. E. A. (2012) Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents. Eur. J. Med. Chem. 52 263–268.
13 Sangaraiah N., Murugan S., Poovan S., Raja R., Alagusundaram P., Ramakrishnan V., and Vellasamy S. (2012) Facile water promoted synthesis of 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids – Highly potent antibacterial agents. Eur. J. Med. Chem. 58 464–469.
14 Dong H.-R., Dong W.-J., Li R.-S., Hu Y.-M., Dong H.-S., and Xie Z.-X. (2014) Synthesis of β-cyanopropan-1-one derivates by domino reaction. Green Chem. 16 (7) 3454–3457.
15 Pokhodylo N.T., Savka R.D., and Obushak M.D. (2014) Synthesis of 3,4-dihydro-2H-thiopyrans and thiopyrano[3,4-с]chromenes having a 1,2,3-triazole substituent by using thionylation–hetero-Diels–Alder domino reaction. Chem. Нeterocycl. Сompd. 50 (4) 544–549.
16 Pokhodylo N.T., Savka R.D., Matiichuk V.S., and Obushak N.D. (2009) Synthesis and selected transformations of 1-(5-methyl-1-aryl-1H‐1,2,3-triazol-4-yl)ethanones and 1-[4-(4-R-5-methyl-1Н-1,2,3-triazol-1-yl)phenyl]ethanones. Russ. J. Gen. Chem. 79 (2) 309–314.
17 Pokhodylo N.T. Shyyka O.Ya., and Obushak M.D. (2018) Convenient synthetic path to ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones. Chem. Нeterocycl. Сompd. 54 (8) 773–779.
18 Pokhodylo N.T. Matiichuk V.S., and Obushak M.D. (2014) Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives. Russ. J. Org. Chem. 50 (2) 275−279.
19 Pokhodylo N.T., and Matiychuk V. S. (2011) Reaction of 1-Aryl-1H-1,2,3-Triazole-4-Carbonyl Chlorides/Isothiocyanates with 3-Amino-5-Methylisoxazole. Phosphorus, Sulfur, Silicon Relat. Elem. 186 (9) 1895–1901.
20 Pokhodylo N.T., Shiika O. Ya., Matiichuk V. S., and Obushak N. D. (2010) Synthesis of [5-(1H-1,2,3-Triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines. Russ. J. Org. Chem. 46 (3) 417–421.
21 Meshkova S.B., Pokhodylo N.T., Doga P.O., and Shyyka, O.Y. (2018) Synthesis and luminescence properties of Eu3+ and Tb3+complexes with pyrazolin-5-one derivatives. Voprosy khimii i khimicheskoi tekhnologii. (2) 30–38.
22 Meshkova S.B., Topilova Z.M., Matiichuk V.S., Pokhodylo N.T., Kovalevskaya I.P., Rakipov I.M., and Doga P.G. (2011) Synthesis and luminescence properties of the Pr(III), Sm(III), Eu(III), Nd(III), and Yb(III) complexes with propane-1,3-dione derivatives. Russ. J. Coord. Chem. 37 (4) 309–315.
23 van Berkel S.S., Brauch S., Gabriel L., Henze M., Stark S., Vasilev D., Wessjohann L.A., Abbas M., and Westermann B. (2012) Traceless tosylhydrazone-based triazole formation: a metal-free alternative to strain-promoted azide-alkyne cycloaddition. Angew. Chem. Int. Ed. 51 (22) 5343–5346.
24 Mindt T. L., and Schibli R. (2007) Cu(I)-Catalyzed Intramolecular Cyclization of Alkynoic Acids in Aqueous Media: A “Click Side Reaction” J. Org. Chem. 72 (26), 10247–10250.
25 Cook T. L., Walker J. A., and Mack J. (2013) Scratching the catalytic surface of mechanochemistry: a multi-component CuAAC reaction using a copper reaction vial. Green Chem. 15 (3) 617–619.
26 Brawn R. A., Welzel M., Lowe J. T., and Panek J. S. (2010) Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes. Org. Lett. 12 (2) 336–339.
27 Ichikawa M., Ohtsuka M., Ohki H., Haginoya N., Itoh M., Usui H., Suzuki M., Terayama K., Kanda A., and Sugita K. (2012). Discovery of novel tricyclic compounds as squalene synthase inhibitors. Bioorg. Med. Chem. 20 (9) 3072–3093.
28 Pokhodylo N. T. Shyyka O. Ya., Matiychuk V. S., Obushak M. D., and Pavlyuk V. V. (2017) A novel base-solvent controlled chemoselective azide attack on an ester group versus keto in alkyl 3-substituted 3-oxopropanoates: Mechanistic insights. ChemistrySelect. 2 (21) 5871–5876.
29 Gangaprasad D., Raj J. P., Kiranmye T., Karthikeyan K., and Elangovan J. (2016) Another example of organo‐click reactions: TEMPO‐promoted oxidative azide–olefin cycloaddition for the synthesis of 1,2,3‐triazoles in water. Eur. J. Org. Chem. 2016 (34) 5642–5646.
30 Gorup A., Kovačič M., Kranjc-Škraba B., Mihelčič B., Simonič S., Stanovnik B., and Tišler M. (1974) Reactions of azidoazolopyridazines with 1,3-dicarbonyl compounds. Tetrahedron 30 (14) 2251 2256.
31 Batog L. V., Rozhkov V. Y., and Struchkova M. I. (2002) Azido-1,2,5-oxadiazoles in reactions with 1,3-dicarbonyl compounds. Mendeleev Commun. 12 (4) 159–161.
32 Ahmadi F., Tisseh Z. N., Dabiri M., and Bazgir A. (2013) Efficient TMG catalyzed synthesis of 1,2,3-triazoles C. R. Chim. 16 (12) 1086–1090.
33 Singh H., Khanna G., and Khurana J. M. (2016) DBU catalyzed metal free synthesis of fused 1,2,3-triazoles through [3+2] cycloaddition of aryl azides with activated cyclic C–H acids. Tetrahedron Lett. 57 (29) 3075 3080.
34 Regitz M., and Schwall H. (1969) Reaktionen CH‐aktiver Verbindungen mit Aziden, XXVI Synthese von α‐Diazo‐iminen und isomeren 1.2.3‐Triazolen sowie deren Umwandlung in α‐Diazo‐immoniumsalze Justus Liebigs Ann. Chem. 728 (1) 99–107.
35 Kumar R., Sharma V., Bua S., Supuran C. T., and Sharma P. K. (2017) Synthesis and biological evaluation of benzenesulphonamide-bearing 1,4,5-trisubstituted-1,2,3-triazoles possessing human carbonic anhydrase I, II, IV, and IX inhibitory activity. J. Enzyme Inhib. Med Chem. 32 (1) 1187–1194.
36 Zhu X.-F., and Shi D.-Q. (2009) Synthesis and biological activities of O‐(E)‐(arylmethyl) 1‐[1‐(arylmethyl)‐5‐methyl‐1H‐1,2,3‐triazol‐4‐yl] ethanone oxime ethers. J. Heterocycl. Chem. 46 (6) 1218–1221.
37 Calderone V., Giorgi I., Livi O., Martinotti E., Mantuano E., Martelli A., and Nardi A. (2005) Benzoyl and/or benzyl substituted 1,2,3-triazoles as potassium channel activators. VIII. Eur. J. Med. Chem. 40 (6) 521–528.
38 Kamalraj V. R., Senthil S., and Kannan P. (2008) One-pot synthesis and the fluorescent behavior of 4-acetyl-5-methyl-1,2,3-triazole regioisomers. J. Mol. Struct. 892 (1 3) 210–215.
2 Pokhodylo N. T., Shyyka O. Ya, Goreshnik E. A., and Obushak M. D. (2020) 4-Phosphonated or 4-free 1,2,3-Triazoles: What controls the Dimroth reaction of arylazides with 2-oxopropylphosphonates? ChemistrySelect, 5 (1) 260–264.
3 Pokhodylo N. T., Shyyka O. Y. Savka, R. D., and Obushak, M. D. (2018) 2-Azido-1,3,4-thiadiazoles, 2-azido-1,3-thiazoles, and aryl azides in the synthesis of 1,2,3-triazole-4-carboxylic acids and their derivatives. Russ. J. Org. Chem. 54 (7) 1090–1099.
4 Pokhodylo N.T., and Matiychuk V. S. (2010) Synthesis of new 1,2,3-triazolo[1,5-a]quinazolinones. J. Heterocyclic Chem. 47 (2) 415–420.
5 Pokhodylo N.T., Matiychuk V.S., and Obushak M.D. (2009) Synthesis of the 1H-1,2,3-triazole derivatives by the cyclization of arylazides with 1-(1,3-benzothiazol-2-yl)acetone, 1,3-benzothiazol-2-ylacetonitrile and (4-aryl-1,3-thiazol-2-yl)acetonitrile. Chem. Heterocycl. Compd. 45 (4) 483–488.
6 Pokhodylo N.T., Matiychuk V.S., and Obushak M.D. (2009) Synthesis of Triazoles via Regioselective Reactions of Aryl Azides with Cyanoacetyl Pyrroles and Indoles. Synthesis (8) 1297–1300.
7 Jasiński R. (2015) Nitroacetylene as dipolarophile in [2 + 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study. Monatsh Chem 146 591–599.
8 Holla B. S., Mahalinga M., Karthikeyan M. S., Poojary B., Akberali P. M., and Kumari N. S. (2005) Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles. Eur. J. Med. Chem. 40 (11) 1173–1178.
9 Keillor J. W., Lubell W., and Pardin C. (2008) Cinnamoyl inhibitors of transglutaminase. WO 2008/144933.
10 Dong H.-S., Wang H.-C., Gao Z.-L., Li R.-S., and Cui F.-H. (2010) Tandem Michael addition/imino‐nitrile cyclization synthesis of 2‐amino‐6‐(1‐aryl‐5‐methyl‐1H‐1,2,3‐triazol‐4-yl)‐4‐phenylpyridine‐3‐carbonitrile. J. Heterocycl. Chem. 47 (2) 389–395.
11 Dong H.-S., Wang Y.-F., Shen G.-L., Dong W.-J., and Quan B. (2012) Synthesis of some new 1‐acyl‐5‐aryl‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐4,5‐dihydro‐1H‐pyrazole. J. Heterocycl. Chem. 49 (1) 149–152.
12 Abdel-Wahab B. F., Mohamed H. A., Abdel-Latif E., and Awad G. E. A. (2012) Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents. Eur. J. Med. Chem. 52 263–268.
13 Sangaraiah N., Murugan S., Poovan S., Raja R., Alagusundaram P., Ramakrishnan V., and Vellasamy S. (2012) Facile water promoted synthesis of 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids – Highly potent antibacterial agents. Eur. J. Med. Chem. 58 464–469.
14 Dong H.-R., Dong W.-J., Li R.-S., Hu Y.-M., Dong H.-S., and Xie Z.-X. (2014) Synthesis of β-cyanopropan-1-one derivates by domino reaction. Green Chem. 16 (7) 3454–3457.
15 Pokhodylo N.T., Savka R.D., and Obushak M.D. (2014) Synthesis of 3,4-dihydro-2H-thiopyrans and thiopyrano[3,4-с]chromenes having a 1,2,3-triazole substituent by using thionylation–hetero-Diels–Alder domino reaction. Chem. Нeterocycl. Сompd. 50 (4) 544–549.
16 Pokhodylo N.T., Savka R.D., Matiichuk V.S., and Obushak N.D. (2009) Synthesis and selected transformations of 1-(5-methyl-1-aryl-1H‐1,2,3-triazol-4-yl)ethanones and 1-[4-(4-R-5-methyl-1Н-1,2,3-triazol-1-yl)phenyl]ethanones. Russ. J. Gen. Chem. 79 (2) 309–314.
17 Pokhodylo N.T. Shyyka O.Ya., and Obushak M.D. (2018) Convenient synthetic path to ethyl 1-aryl-5-formyl-1H-1,2,3-triazole-4-carboxylates and 1-aryl-1,5-dihydro-4H-[1,2,3]triazolo[4,5-d]pyridazin-4-ones. Chem. Нeterocycl. Сompd. 54 (8) 773–779.
18 Pokhodylo N.T. Matiichuk V.S., and Obushak M.D. (2014) Synthesis of 1-(1-aryl-1H-1,2,3-triazol-4-yl)-β-carboline derivatives. Russ. J. Org. Chem. 50 (2) 275−279.
19 Pokhodylo N.T., and Matiychuk V. S. (2011) Reaction of 1-Aryl-1H-1,2,3-Triazole-4-Carbonyl Chlorides/Isothiocyanates with 3-Amino-5-Methylisoxazole. Phosphorus, Sulfur, Silicon Relat. Elem. 186 (9) 1895–1901.
20 Pokhodylo N.T., Shiika O. Ya., Matiichuk V. S., and Obushak N. D. (2010) Synthesis of [5-(1H-1,2,3-Triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines. Russ. J. Org. Chem. 46 (3) 417–421.
21 Meshkova S.B., Pokhodylo N.T., Doga P.O., and Shyyka, O.Y. (2018) Synthesis and luminescence properties of Eu3+ and Tb3+complexes with pyrazolin-5-one derivatives. Voprosy khimii i khimicheskoi tekhnologii. (2) 30–38.
22 Meshkova S.B., Topilova Z.M., Matiichuk V.S., Pokhodylo N.T., Kovalevskaya I.P., Rakipov I.M., and Doga P.G. (2011) Synthesis and luminescence properties of the Pr(III), Sm(III), Eu(III), Nd(III), and Yb(III) complexes with propane-1,3-dione derivatives. Russ. J. Coord. Chem. 37 (4) 309–315.
23 van Berkel S.S., Brauch S., Gabriel L., Henze M., Stark S., Vasilev D., Wessjohann L.A., Abbas M., and Westermann B. (2012) Traceless tosylhydrazone-based triazole formation: a metal-free alternative to strain-promoted azide-alkyne cycloaddition. Angew. Chem. Int. Ed. 51 (22) 5343–5346.
24 Mindt T. L., and Schibli R. (2007) Cu(I)-Catalyzed Intramolecular Cyclization of Alkynoic Acids in Aqueous Media: A “Click Side Reaction” J. Org. Chem. 72 (26), 10247–10250.
25 Cook T. L., Walker J. A., and Mack J. (2013) Scratching the catalytic surface of mechanochemistry: a multi-component CuAAC reaction using a copper reaction vial. Green Chem. 15 (3) 617–619.
26 Brawn R. A., Welzel M., Lowe J. T., and Panek J. S. (2010) Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes. Org. Lett. 12 (2) 336–339.
27 Ichikawa M., Ohtsuka M., Ohki H., Haginoya N., Itoh M., Usui H., Suzuki M., Terayama K., Kanda A., and Sugita K. (2012). Discovery of novel tricyclic compounds as squalene synthase inhibitors. Bioorg. Med. Chem. 20 (9) 3072–3093.
28 Pokhodylo N. T. Shyyka O. Ya., Matiychuk V. S., Obushak M. D., and Pavlyuk V. V. (2017) A novel base-solvent controlled chemoselective azide attack on an ester group versus keto in alkyl 3-substituted 3-oxopropanoates: Mechanistic insights. ChemistrySelect. 2 (21) 5871–5876.
29 Gangaprasad D., Raj J. P., Kiranmye T., Karthikeyan K., and Elangovan J. (2016) Another example of organo‐click reactions: TEMPO‐promoted oxidative azide–olefin cycloaddition for the synthesis of 1,2,3‐triazoles in water. Eur. J. Org. Chem. 2016 (34) 5642–5646.
30 Gorup A., Kovačič M., Kranjc-Škraba B., Mihelčič B., Simonič S., Stanovnik B., and Tišler M. (1974) Reactions of azidoazolopyridazines with 1,3-dicarbonyl compounds. Tetrahedron 30 (14) 2251 2256.
31 Batog L. V., Rozhkov V. Y., and Struchkova M. I. (2002) Azido-1,2,5-oxadiazoles in reactions with 1,3-dicarbonyl compounds. Mendeleev Commun. 12 (4) 159–161.
32 Ahmadi F., Tisseh Z. N., Dabiri M., and Bazgir A. (2013) Efficient TMG catalyzed synthesis of 1,2,3-triazoles C. R. Chim. 16 (12) 1086–1090.
33 Singh H., Khanna G., and Khurana J. M. (2016) DBU catalyzed metal free synthesis of fused 1,2,3-triazoles through [3+2] cycloaddition of aryl azides with activated cyclic C–H acids. Tetrahedron Lett. 57 (29) 3075 3080.
34 Regitz M., and Schwall H. (1969) Reaktionen CH‐aktiver Verbindungen mit Aziden, XXVI Synthese von α‐Diazo‐iminen und isomeren 1.2.3‐Triazolen sowie deren Umwandlung in α‐Diazo‐immoniumsalze Justus Liebigs Ann. Chem. 728 (1) 99–107.
35 Kumar R., Sharma V., Bua S., Supuran C. T., and Sharma P. K. (2017) Synthesis and biological evaluation of benzenesulphonamide-bearing 1,4,5-trisubstituted-1,2,3-triazoles possessing human carbonic anhydrase I, II, IV, and IX inhibitory activity. J. Enzyme Inhib. Med Chem. 32 (1) 1187–1194.
36 Zhu X.-F., and Shi D.-Q. (2009) Synthesis and biological activities of O‐(E)‐(arylmethyl) 1‐[1‐(arylmethyl)‐5‐methyl‐1H‐1,2,3‐triazol‐4‐yl] ethanone oxime ethers. J. Heterocycl. Chem. 46 (6) 1218–1221.
37 Calderone V., Giorgi I., Livi O., Martinotti E., Mantuano E., Martelli A., and Nardi A. (2005) Benzoyl and/or benzyl substituted 1,2,3-triazoles as potassium channel activators. VIII. Eur. J. Med. Chem. 40 (6) 521–528.
38 Kamalraj V. R., Senthil S., and Kannan P. (2008) One-pot synthesis and the fluorescent behavior of 4-acetyl-5-methyl-1,2,3-triazole regioisomers. J. Mol. Struct. 892 (1 3) 210–215.