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Synlett
DOI: 10.1055/a-2759-6590
DOI: 10.1055/a-2759-6590
Letter
Palladium-catalyzed Cyclization of 5-(o-Aminoaryl) 1,2,3-Triazoles with Isocyanides to Construct Triazolo [1,5-c]Quinazolines
Authors
This work was supported by the National Natural Science Foundation of China (21662020).
Abstract
A series of triazoloquinazoline derivatives were synthesized by insertion cyclization of 5-(o-aminoaryl) 1,2,3-triazoles with isocyanides under palladium catalysis. This method features the construction of tricyclic-fused 1,2,3-triazoles involving two C–N bond formations in one simple manipulation. The system is suitable for a variety of 1,2,3-triazoles and isocyanides with good functional group compatibility, and even for other types of nitrogen-containing heterocyclic compounds such as 1,2,4-triazole, pyrazole, tetrazole, imidazole, and indole.
Publication History
Received: 10 September 2025
Accepted after revision: 29 November 2025
Article published online:
13 January 2026
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References
- 1a Aslam M, Rani A, Prajapat A. et al. Coord Chem Rev 2025; 538: 216714
- 1b Luo WJ, Liu Y, Qin H. et al. Eur J Med Chem 2024; 279: 116838
- 1c Nguyen TC, Dung VC, Dau XD. Nat Prod Commun 2025; 20: 1
- 1d Nafie MS, Fahmy SA, Kahwash SH, Diab MK, Dawood KM, Abbas AA. RSC Adv 2025; 15: 5597
- 1e Huang W, Wang YP, Su H. et al. J Agric Food Chem 2024; 72: 21364
- 1f He Y, Yuan D, Yang K, Li B. Molecules 2025; 30: 2099
- 1g Zhao S, Zhang Y, Xu Z. Future Med Chem 2025; 17: 1281
- 2a Dixit D, Verma PK, Marwaha RK. J Iran Chem Soc 2021; 18: 2535
- 2b Petrova AV, Kazakova OB. Int J Mol Sci 2025; 26: 4329
- 2c Sayed MT, Mady MF. Eur J Med Chem 2025; 286: 117270
- 2d Vaishnani MJ, Bijani S, Rahamathulla M. et al. Green Chem Lett Rev 2024; 17: 2307989
- 2e Bhatnagar A, Pakhariya RP, Pemawat G. Top Curr Chem 2025; 27: 383
- 3a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew Chem Int Ed 2002; 41: 2596
- 3b Tornøe CW, Christensen C, Meldal M. J Org Chem 2002; 67: 3057
- 4a Ghosh S, Mohanta N, Gnanaprakasm G. Eur J Org Chem 2024; 27: e202400443
- 4b Kassu M, Zulaut KE, Ross JN, Kirby JE, Manetsch R. ACS Infect Dis 2025; 11: 80
- 4c Antypenko L, Shabelnyk K, Antypenko O. et al. Molecules 2025; 30: 2324
- 4d Mabrouk RR, Mahdy HA, Abdallah AE. et al. Future Med Chem 2025; 17: 529
- 4e Wesseler F, Lohmann S, Riege D. et al. J Med Chem 2022; 65: 15263
- 5a Antypenko LM, Kovalenko SI, Los TS, Rebec OL. J Heterocycl Chem 2017; 54: 1267
- 5b Antipenko L, Karpenko A, Kovalenko S. et al. Chem Pharm Bull 2009; 57: 580
- 6 Al-Salahi R, Al-Omar MA, Alswaidn I, Marzouk M, El-Senousy WM, Ame AE. Res Chem Intermed 2015; 41: 151
- 7a Casale E, Amboldi N, Brasca MG. et al. Bioorg Med Chem 2014; 22: 4135
- 7b Driowya M, Leclercq J, Verones V. et al. Eur J Med Chem 2016; 115: 393
- 8a Zhang H, Jin P, Wang S, Li F, Guan L, Quan Z. Arch Pharm Chem Life Sci 2015; 348: 564
- 8b Zhang C, Yang C, Deng X, Quan Z. Med Chem Res 2021; 21: 3294
- 9a Al-Salahi R, El-Tahir K, Alswaidan I, Lolak N, Hamidaddin M, Marouzk M. Chem Cent J 2014; 8: 3
- 9b Alagarsamy V, Pathak US. Bioorg Med Chem 2007; 15: 3457
- 10 Al-Salahi R, Anouar E, Marzouk M, Taie HAA, Abuelizz HA. Fut Med Chem 2017; 10: 379
- 11a Dai B, Pan Y, Wang X. et al. Adv Synth Catal 2025; 367: e202400851
- 11b Liu S, Wu Y, Zheng J. et al. Org Chem Front 2025; 12: 4757
- 11c Zhang B, Studer A. Chem Soc Rev 2015; 44: 3505
- 11d Liu S, Zheng J, Zhao Z. et al. Org Chem Front 2025; 12: 2643
- 11e Xiong Q, Dong SX, Chen Y, Liu X, Feng X. Nat Commun 2019; 10: 2116
- 11f Li P, Meng X, Yang L, Tang H, Pan Y. Synlett 2018; 29: 2326
- 12a Peng X, Qin F, Xu M. et al. Org Biomol Chem 2019; 17: 8403
- 12b Chen T, Chen J, Tang Y, Zhou J, Guo Y, Chang W. Chin J Chem 2021; 39: 463
- 12c Chen D, Li J, Wang X. et al. Org Chem Front 2022; 9: 4209
- 12d Qiu G, Ding Q, Wu J. Chem Soc Rev 2013; 42: 5257
- 13a Tao S, Zhou J, Liu R, Zhu Y. J Org Chem 2019; 84: 8121
- 13b Song B, Xu B. Chem Soc Rev 2017; 46: 1103
- 13c Gao Q, Li M, Wu W. Chinese J Org Chem 2022; 42: 2659
- 14 Escudero J, Mampuys P, Mensch C. et al. ACS Catal 2022; 12: 6857
- 15 Hommelsheim R, Nahl RV, Hanek LM, Ward JS, Rissanen K, Bolm C. Adv Synth Catal 2024; 366: 717
- 16 Guo X, Wang H, Hu Z. et al. ACS Catal 2025; 15: 5307
- 17a Li J, Zhang S, Xiao T, Yang B, Jiang Y. ChemistrySelect 2024; 9: 637
- 17b Teng L, Wang S, Zhu W. et al. Org Lett 2025; 27: 6895
- 17c Yang B, Zhang S, Dong X, Qin G, Jiang Y. Acta Chim Sin 2023; 81: 1577
- 17d Ma X, Li H, Xin H. et al. Org Lett 2020; 22: 5320
- 18 Vlaar T, Cioc RC, Mampuys P, Maes BUW, Orru RVA, Ruijter E. Angew Chem Int Ed 2012; 51: 13058
- 19 Synthesis of N-(tert-butyl)-[1,2,3] triazolo [1,5-c] quinazolin-5-amines 3: General Procedure. A 10-mL
test tube equipped with a magnetic stir bar was charged with palladium acetate (10
mol%), amines 1 (0.3 mmol), potassium carbonate (0.6 mmol), 30 % hydrogen peroxide
aqueous solution (0.3 mmol), t-butyl isocyanide 2 (0.45 mmol), and acetonitrile (1 mL), and then sealed with a rubber
plug. The solution was stirred at 80 °C for 4 h. After the reaction was completed,
the solvent was evaporated under vacuum, and the crude product was purified by column
chromatography on silica gel (EtOAc/Petrol = 1:6) to give the pure product 3. N-(tert-butyl)-[1,2,3]triazolo[1,5-c]quinazolin-5-amine 3aa White solid, yield (85%). 1H NMR (600 MHz, CDCl3) δ 8.31 (s, 1H), 7.90 (d, J = 7.8 Hz, 1H), 7.72 (d, J = 8.2 Hz, 1H), 7.57 (t, J = 7.7 Hz, 1H), 7.33 (t, J = 7.5 Hz, 1H), 6.43 (s, 1H), 1.67 (s, 9H). 13C NMR (151 MHz, CDCl3) δ 142.3, 139.7, 134.1, 130.8, 126.6, 126.4, 123.9, 123.7, 114.0, 52.7, 29.0. HRMS
(ESI): mass found: 242.1401, calcd mass for C13H15N5
+ [M+H]+: 242.1400.