Abstract
The review is devoted to the use of [1,2,3]triazolo[1,5-a]pyridines as precursors of tautomeric 2-(diazomethyl)pyridines. This methodology represents a convenient tool for the synthesis of various types of nitrogen-containing heterocycles. Both noncatalytic transformations and cascade reactions involving metal carbenes, which have been intensively studied in recent years, are considered. Major approaches to the preparation of [1,2,3]triazolo[1,5-a]pyridines are also summarized in the review.
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REFERENCES
Ford, A., Miel, H., Ring, A., Slattery, C.N., Maguire, A.R., and McKervey, M.A., Chem. Rev., 2015, vol. 115, p. 9981. https://doi.org/10.1021/acs.chemrev.5b00121
Doyle, M.P., Duffy, R., Ratnikov, M., and Zhou, L., Chem. Rev., 2010, vol. 110, p. 704. https://doi.org/10.1021/cr900239n
Gillingham, D. and Fei, N., Chem. Soc. Rev., 2013, vol. 42, p. 4918. https://doi.org/10.1039/C3CS35496B
Zhang, Z. and Wang, J., Tetrahedron, 2008, vol. 64, p. 6577. https://doi.org/10.1016/j.tet.2008.04.074
Davies, H.M.L. and Alford, J.S., Chem. Soc. Rev., 2014, vol. 43, p. 5151. https://doi.org/10.1039/C4CS00072B
Anbarasan, P., Yadagiri, D., and Rajasekar, S., Synthesis, 2014, vol. 46, p. 3004. https://doi.org/10.1055/s-0034-1379303
Bakulev, V., Dehaen, W., and Beryozkina, T., Top. Heterocycl. Chem., 2015, vol. 40, p. 1. https://doi.org/10.1007/7081_2014_131
Jiang, Y., Sun, R., Tang, X.-Y., and Shi, M., Chem. Eur. J., 2016, vol. 22, p. 17910. https://doi.org/10.1002/chem.201601703
Li, Y., Yang, H., and Zhai, H., Chem. Eur. J., 2018, vol. 24, p. 12757. https://doi.org/10.1002/chem.201800689
Li, W. and Zhang, J., Chem. Eur. J., 2020, vol. 26, p. 11931. https://doi.org/10.1002/chem.202000674
LʼAbbe, G., Van Stappen, P., and Toppet, S., Tetrahedron, 1985, vol. 41, p. 4621. https://doi.org/10.1016/S0040-4020(01)82357-7
LʼAbbé, G., Luyten, I., Vercauteren, K., and Dehaen, W., Bull. Soc. Chim. Belg., 1993, vol. 102, p. 683. https://doi.org/10.1002/bscb.19931021010
Kotovshchikov, Y.N., Latyshev, G.V., Navasardyan, M.A., Erzunov, D.A., Beletskaya, I.P., and Lukashev, N.V., Org. Lett., 2018, vol. 20, p. 4467. https://doi.org/10.1021/acs.orglett.8b01755
Kotovshchikov, Y.N., Latyshev, G.V., Kirillova, E.A., Moskalenko, U.D., Lukashev, N.V., and Beletskaya, I.P., J. Org. Chem., 2020, vol. 85, p. 9015. https://doi.org/10.1021/acs.joc.0c00931
Gevondian, G.A., Kotovshchikov, Y.N., Latyshev, G.V., Lukashev, N.V., and Beletskaya, I.P., J. Org. Chem., 2021, vol. 86, p. 5639. https://doi.org/10.1021/acs.joc.1c00115
Yadagiri, D., Rivas, M., and Gevorgyan, V., J. Org. Chem., 2020, vol. 85, p. 11030. https://doi.org/10.1021/acs.joc.0c01652
Filippov, I.P., Titov, G.D., and Rostovskii, N.V., Synthesis, 2020, vol. 52, p. 3564. https://doi.org/10.1055/s-0040-1707254
Abarca, B., Ballesteros, R., and Elmasnaouy, M., Tetrahedron, 1998, vol. 54, p. 15287. https://doi.org/10.1016/S0040-4020(98)00955-7
Zimmerman, H.E. and Ignatchenko, A., J. Org. Chem., 1999, vol. 64, p. 6635. https://doi.org/10.1021/jo990323h
Frick, J.J., Ly, C.Q., and Schwarz, J.B., Synthesis, 2015, vol. 47, p. 2593. https://doi.org/10.1055/s-0034-1379932
Mine, S., Kawamura, S., and Nakagawa, K., Synth. Commun., 1976, vol. 6, p. 69. https://doi.org/10.1080/00397917608072611
Prakash, O., Gujral, H.K., Rani, N., and Singh, S.P., Synth. Commun., 2000, vol. 30, p. 417. https://doi.org/10.1080/00397910008087337
Hirayama, T., Ueda, S., Okada, T., Tsurue, N., Okuda, K., and Nagasawa, H., Chem. Eur. J., 2014, vol. 20, p. 4156. https://doi.org/10.1002/chem.201302997
Xu, P. and Xu, H.-C., ChemElectroChem, 2019, vol. 6, p. 4177. https://doi.org/10.1002/celc.201900080
Boyer, J. and Goebel, N., J. Org. Chem., 1960, vol. 25, p. 304. https://doi.org/10.1021/jo01072a634
Shang, Z.-H., Zhang, Z.-X., Weng, W.-Z., Wang, Y.-F., Cheng, T.-W., Zhang, Q.-Y., Song, L.-Q., Shao, T.-Q., Liu, K.-X., and Zhu, Y.-P., Adv. Synth. Catal., 2021, vol. 363, p. 490. https://doi.org/10.1002/adsc.202001052
Regitz, M., Angew. Chem. Int. Ed., 1965, vol. 4, p. 431. https://doi.org/10.1002/anie.196504311
Cai, Y.-M., Zhang, X., An, C., Yang, Y.-F., Liu, W., Gao, W.-X., Huang, X.-B., Zhou, Y.-B., Liu, M.-C., and Wu, H.-Y., Org. Chem. Front., 2019, vol. 6, p. 1481. https://doi.org/10.1039/C9QO00071B
Abarca-González, B., J. Enzyme Inhib. Med. Chem., 2002, vol. 17, p. 359. https://doi.org/10.1080/1475636021000005622
Jones, G., Adv. Heterocycl. Chem., 2002, vol. 83, p. 1. https://doi.org/10.1016/S0065-2725(02)83003-3
Jones, G. and Abarca, B., Adv. Heterocycl. Chem., 2010, vol. 100, p. 195. https://doi.org/10.1016/S0065-2725(10)10007-5
Jones, G. and Sliskovic, D.R., Tetrahedron Lett., 1980, vol. 21, p. 4529. https://doi.org/10.1016/S0040-4039(00)74542-4
Blanco, F., Alkorta, I., Elguero, J., Cruz, V., Abarca, B., and Ballesteros, R., Tetrahedron, 2008, vol. 64, p. 11150. https://doi.org/10.1016/j.tet.2008.09.064
Abarca, B., Ballesteros, R., Mojarred, F., Jones, G., and Mouat, D.J., J. Chem. Soc. Perkin 1, 1987, p. 1865. https://doi.org/10.1039/P19870001865
Bentabed-Ababsa, G., Blanco, F., Derdour, A., Mongin, F., Trécourt, F., Quéguiner, G., Ballesteros, R., and Abarca, B., J. Org. Chem., 2009, vol. 74, p. 163. https://doi.org/10.1021/jo801675h
Jones, G., Mouat, D.J., Pitman, M.A., Lunt, E., and Lythgoe, D.J., Tetrahedron, 1995, vol. 51, p. 10969. https://doi.org/10.1016/0040-4020(95)00652-O
Chiassai, L., Adam, R., Drechslerová, M., Ballesteros, R., and Abarca, B., J. Fluor. Chem., 2014, vol. 164, p. 44. https://doi.org/10.1016/j.jfluchem.2014.05.001
Adam, R., Abarca, B., and Ballesteros, R., Synthesis, 2017, vol. 49, p. 5059. https://doi.org/10.1055/s-0036-1588525
Abarca, B., Ballesteros, R., Blanco, F., Bouillon, A., Collot, V., Domı́nguez, J.-R., Lancelot, J.-C., and Rault, S., Tetrahedron, 2004, vol. 60, p. 4887. https://doi.org/10.1016/j.tet.2004.03.083
Abarca, B., Aucejo, R., Ballesteros, R., Blanco, F., and García-España, E., Tetrahedron Lett., 2006, vol. 47, p. 8101. https://doi.org/10.1016/j.tetlet.2006.09.051
Liu, S., Sawicki, J., and Driver, T.G., Org. Lett., 2012, vol. 14, p. 3744. https://doi.org/10.1021/ol301606y
Rawat, D., Kumar, R., and Adimurthy, S., Eur. J. Org. Chem., 2019, vol. 2019, p. 7874. https://doi.org/10.1002/ejoc.201901748
Tennant, G. and Vevers, R.J.S., J. Chem. Soc., Chem. Commun., 1974, p. 671b. https://doi.org/10.1039/C3974000671B
L’abbé, G., Godts, F., and Toppet, S., J. Chem. Soc., Chem. Commun., 1985, p. 589. https://doi.org/10.1039/C39850000589
Aylward, N., Winter, H.-W., Eckhardt, U., and Wentrup, C., J. Org. Chem., 2016, vol. 81, p. 667. https://doi.org/10.1021/acs.joc.5b02639
Abarca, B., Alkorta, I., Ballesteros, R., Blanco, F., Chadlaoui, M., Elguero, J., and Mojarrad, F., Org. Biomol. Chem., 2005, vol. 3, p. 3905. https://doi.org/10.1039/B510535H
Boyer, J.H. and Wolford, L.T., J. Am. Chem. Soc., 1958, vol. 80, p. 2741. https://doi.org/10.1021/ja01544a040
Jones, G., Mouat, D.J., and Tonkinson, D.J., J. Chem. Soc. Perkin 1, 1985, p. 2719. https://doi.org/10.1039/P19850002719
Wentrup, C., Tetrahedron, 1974, vol. 30, p. 1301. https://doi.org/10.1016/S0040-4020(01)97303-X
Wentrup, C., Helv. Chim. Acta, 1978, vol. 61, p. 1755. https://doi.org/10.1002/hlca.19780610522
Adam, R., Alom, S., Abarca, B., and Ballesteros, R., Tetrahedron, 2016, vol. 72, p. 8436. https://doi.org/10.1016/j.tet.2016.11.006
Kuhn, A., Plüg, C., and Wentrup, C., J. Am. Chem. Soc., 2000, vol. 122, p. 1945. https://doi.org/10.1021/ja993859t
Plüg, C., Kuhn, A., and Wentrup, C., J. Chem. Soc. Perkin 1, 2002, p. 1366. https://doi.org/10.1039/B202523J
Dong, C., Wang, X., Pei, Z., and Shen, R., Org. Lett., 2019, vol. 21, p. 4148. https://doi.org/10.1021/acs.orglett.9b01334
Kuzaj, M., Lüerssen, H., and Wentrup, C., Angew. Chem. Int. Ed., 1986, vol. 25, p. 480. https://doi.org/10.1002/anie.198604801
Tomioka, H., Ichikawa, N., and Komatsu, K., J. Am. Chem. Soc., 1993, vol. 115, p. 8621. https://doi.org/10.1021/ja00072a015
Zhang, Z., Yadagiri, D., and Gevorgyan, V., Chem. Sci., 2019, vol. 10, p. 8399. https://doi.org/10.1039/C9SC02448D
Chuprakov, S., Hwang, F.W., and Gevorgyan, V., Angew. Chem. Int. Ed., 2007, vol. 46, p. 4757. https://doi.org/10.1002/anie.200700804
Chuprakov, S. and Gevorgyan, V., Org. Lett., 2007, vol. 9, p. 4463. https://doi.org/10.1021/ol702084f
Wang, C., Zhou, Y., and Bao, X., J. Org. Chem., 2017, vol. 82, p. 3751. https://doi.org/10.1021/acs.joc.7b00204
Kim, H., Kim, S., Kim, J., Son, J.-Y., Baek, Y., Um, K., and Lee, P.H., Org. Lett., 2017, vol. 19, p. 5677. https://doi.org/10.1021/acs.orglett.7b02826
Shi, Y., Gulevich, A.V., and Gevorgyan, V., Angew. Chem. Int. Ed., 2014, vol. 53, p. 14191. https://doi.org/10.1002/anie.201408335
Lv, X., Yang, H., Shi, T., Xing, D., Xu, X., and Hu, W., Adv. Synth. Catal., 2019, vol. 361, p. 1265. https://doi.org/10.1002/adsc.201801497
Dequina, H.J., Eshon, J., Raskopf, W.T., Fernández, I., and Schomaker, J.M., Org. Lett., 2020, vol. 22, p. 3637. https://doi.org/10.1021/acs.orglett.0c01124
Filippov, I.P., Novikov, M.S., Khlebnikov, A.F., and Rostovskii, N.V., Eur. J. Org. Chem., 2020, vol. 2020, p. 2904. https://doi.org/10.1002/ejoc.202000210
Xu, G., Shao, Y., Tang, S., Chen, Q., and Sun, J., Org. Lett., 2020, vol. 22, p. 9303. https://doi.org/10.1021/acs.orglett.0c03533
Kim, J.H., Gensch, T., Zhao, D., Stegemann, L., Strassert, C.A., and Glorius, F., Angew. Chem. Int. Ed., 2015, vol. 54, p. 10975. https://doi.org/10.1002/anie.201504757
Zhao, D., Kim, J.H., Stegemann, L., Strassert, C.A., and Glorius, F., Angew. Chem. Int. Ed., 2015, vol. 54, p. 4508. https://doi.org/10.1002/anie.201411994
Jeon, W.H., Son, J.-Y., Kim, J.E., and Lee, P.H., Org. Lett., 2016, vol. 18, p. 3498. https://doi.org/10.1021/acs.orglett.6b01750
Dong, Y., Chen, J., Cui, Y., Bao, L., and Xu, H., Org. Lett., 2020, vol. 22, p. 772. https://doi.org/10.1021/acs.orglett.9b03904
Xu, H.-B., Zhu, Y.-Y., and Dong, L., J. Org. Chem., 2019, vol. 84, p. 16286. https://doi.org/10.1021/acs.joc.9b02468
Helan, V., Gulevich, A.V., and Gevorgyan, V., Chem. Sci., 2015, vol. 6, p. 1928. https://doi.org/10.1039/C4SC03358B
Shi, Y. and Gevorgyan, V., Chem. Commun., 2015, vol. 51, p. 17166. https://doi.org/10.1039/C5CC07598J
Joshi, A., Mohan, D.C., and Adimurthy, S., Org. Lett., 2016, vol. 18, p. 464. https://doi.org/10.1021/acs.orglett.5b03509
Shen, R., Dong, C., Yang, J., and Han, L., Adv. Synth. Catal., 2018, vol. 360, p. 4252. https://doi.org/10.1002/adsc.201800909
Moon, Y., Kwon, S., Kang, D., Im, H., and Hong, S., Adv. Synth. Catal., 2016, vol. 358, p. 958. https://doi.org/10.1002/adsc.201500967
AbuSalim, D.I., Hong, S., and Baik, M.-H., Chem. Asian J., 2018, vol. 13, p. 2505. https://doi.org/10.1002/asia.201800498
Joshi, A., Semwal, R., Suresh, E., and Adimurthy, S., Chem. Commun., 2019, vol. 55, p. 10888. https://doi.org/10.1039/C9CC05953A
Xin, L., Wan, W., Yu, Y., Wan, Q., Ma, L., and Huang, X., ACS Catal., 2021, vol. 11, p. 1570. https://doi.org/10.1021/acscatal.0c05156
Roy, S., Das, S.K., and Chattopadhyay, B., Angew. Chem. Int. Ed., 2018, vol. 57, p. 2238. https://doi.org/10.1002/anie.201711209
Dzik, W.I., Xu, X., Zhang, X.P., Reek, J.N.H., and de Bruin, B., J. Am. Chem. Soc., 2010, vol. 132, p. 10891. https://doi.org/10.1021/ja103768r
Lu, H., Dzik, W.I., Xu, X., Wojtas, L., de Bruin, B., Zhang, X.P., J. Am. Chem. Soc., 2011, vol. 133, p. 8518. https://doi.org/10.1021/ja203434c
Zhang, Z. and Gevorgyan, V., Org. Lett., 2020, vol. 22, p. 8500. https://doi.org/10.1021/acs.orglett.0c03099
Rawat, D., Ravi, C., Joshi, A., Suresh, E., Jana, K., Ganguly, B., and Adimurthy, S., Org. Lett., 2019, vol. 21, p. 2043. https://doi.org/10.1021/acs.orglett.9b00180
Wang, H., Cai, S., Ai, W., Xu, X., Li, B., and Wang, B., Org. Lett., 2020, vol. 22, p. 7255. https://doi.org/10.1021/acs.orglett.0c02586
Joshi, A., Mohan, D.C., and Adimurthy, S., J. Org. Chem., 2016, vol. 81, p. 9461. https://doi.org/10.1021/acs.joc.6b01742
Opsomer, T., Van Hoof, M., D’Angelo, A., and Dehaen, W., Org. Lett., 2020, vol. 22, p. 3596. https://doi.org/10.1021/acs.orglett.0c01069
Zhang, G.-T., Zhang, J., Xu, Y.-J., and Dong, L., Eur. J. Org. Chem., 2018, vol. 2018, p. 4197. https://doi.org/10.1002/ejoc.201800764
Lamaa, D., Lin, H.-P., Bzeih, T., Retailleau, P., Alami, M., and Hamze, A., Eur. J. Org. Chem., 2019, vol. 2019, p. 2602. https://doi.org/10.1002/ejoc.201801803
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1084–1119 https://doi.org/10.31857/S0514749221080024.
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Kotovshchikov, Y.N., Voloshkin, V.A., Latyshev, G.V. et al. Cascade Transformations of [1,2,3]Triazolo[1,5-a]pyridines as Convenient Precursors of Diazo Compounds and Metal Carbenes. Russ J Org Chem 57, 1212–1244 (2021). https://doi.org/10.1134/S1070428021080029
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DOI: https://doi.org/10.1134/S1070428021080029