Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
Yaroslavl, Yaroslavl, Russian Federation
The article considers the new method of producing 4-aryl-6-haloquinazolines by transforming 5-halogen-3-aryl-2,1-benzisoxazoles by reacting them with urotropin in a polyphosphoric acid medium.
transformation, 5-halogen-3-aryl-2,1-benzisoxazoles, urotropin, 4-aryl-6-haloquinazolines
1. Pantyukhin A.A., Pershina N.N., Balandina S.A., Aleksandrova G.A., Makhmudov R.R., Mikhailovskii A.G. Synthesis and analgesic and antimicrobial activity of 2-aroylcyclohexanones and 3-aryl-4,5,6,7-tetrahydro-2,1-benzisoxazoles. Pharmaceutical Chemistry Journal. 2013. V. 47. N 4. P. 195–197. DOI:https://doi.org/10.1007/s11094-013-0925-2.
2. Chaker A., Najahi E., Chatriant O., Valentin A., Téné N., Treilhou M., Chabchoub F., Nepveu F. New 3-substituted-2,1-benzisoxazoles: Synthesis and antimicrobial activities. Arabian Journal of Chemistry. 2017. V. 10. P. S2464-S2470. DOI:https://doi.org/10.1016/j.arabjc.2013.09.011.
3. Tan P.W., Seayad J. Advances in amide and thioamide assisted C(sp3)-H functionalization. Tetrahedron Letters. 2019. V. 60. N 50. P. 151338. DOI:https://doi.org/10.1016/j.tetlet.2019.151338.
4. Li J., Tan E., Keller N., Chen Y.-H., Zehetmaier P.M., Jakowetz A.C., Bein T., Knochel P. Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines. J. Am. Chem. Soc. 2019. V. 141. N 1. P. 98–103. DOI:https://doi.org/10.1021/jacs.8b11466.
5. Kotov A.D., Proskurina I.K. Antraniles (2,1-benzisoxazoles) as aminating agents. Chemistry of Heterocyclic Compounds. 2019. V. 55. N 8. P. 698-700. DOI:https://doi.org/10.1007/s10593-019-02523-4.
6. Xie F., Shen B., Li X. Enantioselective Copper-Catalyzed Hydroamination of Vinylarenes with Anthranils. Org. Lett. 2018. V. 20. N 22. P. 7154-7157. DOI:https://doi.org/10.1021/acs.orglett.8b03093.
7. Kim S., Han S.H., Mishra N.K., Chun R., Jung Y.H., Kim H.S., Park J.S., Kim I.S. Dual Role of Anthranils as Amination and Transient Directing Group Sources: Synthesis of 2-Acyl Acridines. Org. Lett. 2018. V. 20. N 13. P. 4010-4014. DOI:https://doi.org/10.1021/acs.orglett.8b01571.
8. Sheng J., He R., Xue J., Wu C., Qiao J., Chen C. Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds. Org. Lett. 2018. V. 20. N 15. P. 4458 4461. DOI:https://doi.org/10.1021/acs.orglett.8b01748.
9. Serrano J.L., Soeiro P.F., Reis M.A., Boto R.E.F., Silvestre S., Almeida P. Synthesis and process optimization of symmetric and unsymmetric barbiturates C5-coupled with 2,1-benzisoxazoles. Mol. Divers. 2020. V. 24. N 1. P. 155–166. DOI:https://doi.org/10.1007/s11030-019-09937-4.
10. Wang Y., Yu P., Ren Q., Jia F., Chen Y., Wu A. Synthesis of 2,1-Benzoisoxazole-Containing 1,2,3-Triazoles through Copper-Catalyzed Three-Component Domino Reactions of o-Bromoacetophenones, Aldehydes, and Sodium Azide. J. Org. Chem. 2020. V. 85. N 4. P. 2688–2696. DOI:https://doi.org/10.1021/acs.joc.9b02865.
11. Begunov R.S., Sokolov A.A. Sposob sinteza 1,2,4,5-tetrakis(benzazol)benzolov. Ot himii k tehnologii shag za shagom. 2021. T.2. Vyp. 3. S. 61-65. DOI:https://doi.org/10.52957/27821900_2021_03_61.
12. Kabanova M. V., Makarova E. S., Chirkova Zh. V., Filimonov S. I. Uproschennyy metod polucheniya 3-bromindol-5,6-dikarbonitrilov iz 1-gidroksindol-5,6-dikarbonitrilov Ot himii k tehnologii shag za shagom. 2021. T.2. Vyp. 3. S. 24-28. DOI:https://doi.org/10.52957/27821900_2021_01_24.
13. Bastrakov M.A., Fedorenko A.K., Starosotnikov A.M. Synthesis of 6-R-isoxazolo[4,3-b]pyridines and their reactions with C-nucleophiles. Russ. Chem. Bull. 2020. V. 69. N 2. P. 394–397. DOI:https://doi.org/10.1007/s11172-020-2774-y.
14. Ganzha V.V., Kotov A.D., Sokolov V.G., Orlov V.Y. Direct amination of 5-halo-3-phenyl-2,1-benzisoxazoles. Russ. J. Org. Chem. 2006. V. 42. N 8. P. 1248–1249. DOI:https://doi.org/10.1134/S107042800608029X.
15. Orlov V.Y., Ganzha V.V., Kotov A.D., Sokolov V.G. Synthesis of nitroacridinones from 2,1-benzisoxazole derivatives. Russ. J. Org. Chem. 2007. V. 43. N 10. P. 1502–1507. DOI:https://doi.org/10.1134/S1070428007100168.
16. Lei X., Gao M., Tang Y. Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles. Org. Lett. 2016. V. 18. N 19. P. 4990–4993. DOI:https://doi.org/10.1021/acs.orglett.6b02454.
17. Dabiri M., Salehi P., Bahramnejad M. Ecofriendly and Efficient One-Pot Procedure for the Synthesis of Quinazoline Derivatives Catalyzed by an Acidic Ionic Liquid Under Aerobic Oxidation Conditions. Synthetic Communications. 2010. V. 40. N 21. P. 3214-3225. DOI:https://doi.org/10.1080/00397910903395250.
18. Awad M.K., Abdel-Aal M.F., Atlam F.M., Hekal H.A. Molecular docking, molecular modeling, vibrational and biological studies of some new heterocyclic α-aminophosphonates. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy. 2019. V. 206. P. 78–88. DOI:https://doi.org/10.1016/j.saa.2018.07.083.
