A facile method for building fused quinoxaline-quinolinones via an acidless post-Ugi cascade reaction
- Corresponding author: Zhong-Zhu Chen, 18883138277@163.com Chuan Xu, 1535486239@qq.com
Citation: Yong Li, Jie Lei, Jia Xu, Dian-Yong Tang, Zhong-Zhu Chen, Jin Zhu, Chuan Xu. A facile method for building fused quinoxaline-quinolinones via an acidless post-Ugi cascade reaction[J]. Chinese Chemical Letters, ;2017, 28(3): 541-545. doi: 10.1016/j.cclet.2016.10.027
(a) E. Ruijter, R. Scheffelaar, R.V. Orru, Multicomponent reaction design in the quest for molecular complexity and diversity, Angew. Chem. Int. Ed. 50(2011) 6234-6246;
(b) R.K. Li, Q.L. Yang, Y. Liu, et al., A novel and green synthesis of indolone-Namino acid derivatives via the Passerini three-component reactions in water, Chin. Chem. Lett. 27(2016) 345-348.
(a) C.G. Neochoritis, J. Zhang, A. Dömling, Leuckart-Wallach approach to sugar isocyanides and its iMCRs, Synthesis 47(2015) 2407-2413;
(b) Z. Hossaini, Solvent-free synthesis of substituted five membered heterocycles:one-pot reaction of primary amine and alkyl propiolate or isothiocyanate in the presence of oxalyl chloride, Chin. Chem. Lett. 25(2014) 159-162;
(c) U.K. Sharma, N. Sharma, D.D. Vachhani, E.V.V. Eycken, Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds, Chem. Soc. Rev. 44(2015) 1836-1860;
(d) G. Koopmanschap, E. Ruijter, R.V. Orru, Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics, Beilstein J. Org. Chem. 10(2014) 544-598.
(a) B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Small heterocycles in multicomponent reactions, Chem. Rev. 114(2014) 8323-8359;
(b) Z. Hossaini, F. Rostami-Charati, S. Seyfi, M. Ghambarian, Multicomponent reactions for the synthesis of functionalized 1, 4-oxathiane-3-thiones under microwave irradiation in water, Chin. Chem. Lett. 24(2013) 376-378;
(c) G.R. Kuethe, J.T. Kuethe, Practical methodologies for the synthesis of indoles, Chem. Rev. 106(2006) 2875-2911.
(a) A. Dömling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39(2000) 3168-3210;
(b) A. Dömling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106(2006) 17-89.
Patil P., Zhang J., Kurpiewska K., Kalinowska-Tłuścik J., Dömling A.. Hydrazine in the Ugi tetrazole reaction[J]. Synthesis, 2016,48:1122-1130. doi: 10.1055/s-00000084
Dömling A., Wang W., Wang K.. Chemistry and biology of multicomponent reactions[J]. Chem. Rev., 2012,112:3083-3135. doi: 10.1021/cr100233r
Sharma N., Li Z., Sharma U.K., Van der Eycken E.V.. Facile access to functionalized spiro[indoline-3, 2'-pyrrole]-2, 5'-diones via post-Ugi domino Buchwald-Hartwig/Michael reaction[J]. Org. Lett., 2014,16:3884-3887. doi: 10.1021/ol5019079
Kalinski C., Umkehrer M., Schmidt J.. A novel one-pot synthesis of highly diverse indole scaffolds by the Ugi/Heck reaction[J]. Tetrahedron Lett., 2006,47:4683-4686. doi: 10.1016/j.tetlet.2006.04.127
Xu Z., De Moliner F., Cappelli A.P., Hulme C.. Aldol reactions in multicomponent reaction based domino pathways:a multipurpose enabling tool in heterocyclic chemistry[J]. Org. Lett., 2013,15:2738-2741. doi: 10.1021/ol401068u
Xu Z., De Moliner F., Cappelli A.P., Hulme C.. Ugi/aldol sequence:expeditious entry to several families of densely substituted nitrogen heterocycles[J]. Angew. Chem. Int. Ed., 2012,51:8037-8040. doi: 10.1002/anie.v51.32
Kumar A., Li Z., Sharma S.K., Parmar V.S., Van der Eycken E.V.. An expedient route to imidazo[1, 4] diazepin-7-ones via a post-Ugi gold-catalyzed heteroannulation[J]. Org. Lett., 2013,15:1874-1877. doi: 10.1021/ol400526a
Nicholas B.V., Bai F., Perez C.. Phenazine antibiotic inspired discovery of potent bromophenazine antibacterial agents against Staphylococcus aureus and Staphylococcus epidermidis[J]. Org. Biomol. Chem., 2014,12:881-886. doi: 10.1039/c3ob42416b
Conda-Sheridan M., Marler L., Park E.J.. Potential chemopreventive agents based on the structure of the lead compound 2-bromo-1-hydroxyphenazine, isolated from streptomyces species, strain CNS284[J]. J. Med. Chem., 2010,53:8688-8699. doi: 10.1021/jm1011066
Zeghida W., Debray J., Chierici S., Dumy P., Demeunynck M.. Concise synthesis of 2-amino-4(3H)-quinazolinones from simple (hetero) aromatic amines[J]. J. Org. Chem., 2008,73:2473-2475. doi: 10.1021/jo7026883
Shekhar A.C., Rao P.S., Narsaiah B., Allanki D.A., Sijwali P.S.. Emergence of pyrido quinoxalines as new family of antimalarial agents[J]. Eur. J. Med. Chem., 2014,77:280-287. doi: 10.1016/j.ejmech.2014.03.010
Pendergast W., Johnson J.V., Dickerson S.H.. Benzoquinazoline inhibitors of thymidylate synthase:enzyme inhibitory activity and cytotoxicity of some 3-amino-and 3-methylbenzo[f]quinazolin-1(2H)-ones[J]. J. Med. Chem., 1993,36:2279-2291. doi: 10.1021/jm00068a004
Chern J.W., Tao P.L., Wang K.C.. Studies on quinazolines and 1, 2, 4-benzothiadiazine 1. 1-dioxides. 8.1, 2 Synthesis and pharmacological evaluation of tricyclic fused quinazolines and 1, 2, 4-benzothiadiazine 1, 1-dioxides as potential alpha1-adrenoceptor antagonists[J]. J. Med. Chem., 1998,41:3128-3141. doi: 10.1021/jm970159v
Grosso J.A., Nichols E.D., Kohli J.D., Glock D.. Synthesis of 2-(alkylamino)-5, 6-and -6, 7-dihydroxy-3, 4-dihydroquinazolines and evaluation as potential dopamine agonists[J]. J. Med. Chem., 1982,25:703-708. doi: 10.1021/jm00348a018
Song G., Li S., Yang Z.. Microwave-assisted synthesis of fused piperazinebenzimidazoles via a facile, one-pot procedure[J]. Tetrahedron Lett., 2015,56:4616-4618. doi: 10.1016/j.tetlet.2015.06.035
Ou T., Lu Y., Tan J.. G-quadruplexes:targets in anticancer drug design[J]. ChemMedChem, 2008,3:690-713. doi: 10.1002/(ISSN)1860-7187
L. El Kaïm, L. Grimaud, Isocyanide Chemistry:Ugi and Passerini Reactions with Carboxylic Acid Surrogates, Wiley-VCH, Weinheim, 2012, pp. 159-194.
Avaz M., Martinez-Ariza G., Hulme C.. A robust protocol for the synthesis of quinoxalines and 5H-benzo[e][1, 4] di-azepines via the acidless Ugi reaction[J]. Synlett, 2014,25:1680-1684. doi: 10.1055/s-00000083
Pan S., List B.. Catalytic three-component Ugi reaction[J]. Angew. Chem. Int. Ed., 2008,47:3622-3625. doi: 10.1002/(ISSN)1521-3773
Chen Z., Zhang J., Tang D., Xu Z.. Synthesis of fused benzimidazole-quinoxalinones via UDC strategy and following the intermolecular nucleophilic substitution reaction[J]. Tetrahedron Lett., 2014,55:2742-2744. doi: 10.1016/j.tetlet.2014.03.063
Xu Z., De Moliner F., Cappelli A.P., Hulme C.. Aldol reactions in multicomponent reaction based domino pathways:a multipurpose enabling tool in heterocyclic chemistry[J]. Org. Lett., 2013,15:2738-2741. doi: 10.1021/ol401068u
Bhattacharya D., Mitra S., Chattopadhyay P.. A rapid one pot synthetic approach towards imidazole fused benzodiazepinone using Ugi reaction strategy[J]. Synthesis, 2015,47:2294-2298. doi: 10.1055/s-00000084
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