2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Mediated Tandem Oxidative-Coupling/Annulation of o-Hydroxyaryl Enaminones with Cycloheptatriene

Abstract

A DDQ-mediated tandem reaction of easily available o-hydroxy­aryl enaminones and cycloheptatriene is disclosed. It provides an effective and convenient method for the synthesis of 3-(cycloheptatrienyl)-substituted chromones in moderate to excellent yields with good functional group tolerance; this reaction involves an oxidative coupling and intramolecular annulation pathway.

Key words

annulation - alkylation - DDQ - o-hydroxyaryl enaminones - cycloheptatriene

Publikationsverlauf

Eingereicht: 26. September 2020

Angenommen nach Revision: 15. Oktober 2020

Artikel online veröffentlicht:
11. November 2020

• References

• 1a Khan KM, Ambreen N, Mughal UR, Jalil S, Perveen S, Choudhary MI. Eur. J. Med. Chem. 2010; 45: 4058
• 1b Silva CF. M, Pinto DC. G. A, Silva AM. S. ChemMedChem 2016; 11: 2252
• 2 Han SH, Kim S, De U, Mishra NK, Park J, Sharma S, Kwak JH, Han S, Kim HS, Kim IS. J. Org. Chem. 2016; 81: 12416
• 3a Gomes A, Neuwirth O, Freitas M, Couto D, Ribeiro D, Figueiredo AG. P. R, Silva AM. S, Seixas RS. G. R, Pinto DC. G. A, Tomé AC, Cavaleiro JA. S, Fernandes E, Lima JL. F. C. Bioorg. Med. Chem. 2009; 17: 7218
• 3b Kuroda M, Uchida S, Watanabe K, Mimaki Y. Phytochemistry 2009; 70: 288
• 4 Nazhand A, Durazzo A, Lucarini M, Romano R, Mobilia MA, Izzo AA, Santini A. Nat. Prod. Res. 2019; 34: 137
• 5 Zhou T, Shi Q, Chen C.-H, Zhu H, Huang L, Ho P, Lee K.-H. Bioorg. Med. Chem. 2010; 18: 6678
• 6a Gaspar A, Matos MJ, Garrido J, Uriarte E, Borges F. Chem. Rev. 2014; 114: 4960
• 6b Frasinyuk MS, Mrug GP, Bondarenko SP, Sviripa VM, Zhang W, Cai X.-F, Fiandalo MV, Mohler JL, Liu C, Watt DS. Org. Biomol. Chem. 2015; 13: 11292
• 6c Frasinyuk MS, Mrug GP, Bondarenko SP, Khilya VP, Sviripa VM, Syrotchuk OA, Zhang W, Cai X, Fiandalo MV, Mohler JL, Liu C, Watt DS. ChemMedChem 2016; 11: 600
• 6d Vavsari VF, Balalaie S. Chem. Heterocycl. Compd. 2020; 56: 404
• 7a Yokoe I, Sugita Y, Shirataki Y. Chem. Pharm. Bull. 1989; 37: 529
• 7b Patonay T, Vasas A, Kiss-Szikszai A, Silva AM. S, Cavaleiro JA. S. Aust. J. Chem. 2010; 63: 1582
• 7c Yang Q, Zhang Z, Liang B. J. Heterocycl. Chem. 2015; 51: 310
• 8a Bolós J, Gubert S, Anglada L, Planas JM, Burgarolas C, Castelló JM, Sacristán A, Ortiz JA. J. Med. Chem. 1996; 39: 2962
• 8b Vasselin DA, Westwell AD, Matthews CS, Bradshaw TD, Stevens MF. G. J. Med. Chem. 2006; 49: 3973
• 8c Wan J.-P, Pan Y.-J. Chem. Commun. 2009; 2768
• 8d Xiang H, Yang C. Org. Lett. 2014; 16: 5686
• 8e Bornadiego A, Díaz J, Marcos CF. Adv. Synth. Catal. 2014; 356: 718
• 8f Akram MO, Bera S, Patil NT. Chem. Commun. 2016; 52: 12306
• 8g Xiang H, Zhao Q, Tang Z, Xiao J, Xia P, Wang C, Yang C, Chen X, Yang H. Org. Lett. 2017; 19: 146
• 8h Guo Y, Xiang Y, Wei L, Wan J.-P. Org. Lett. 2018; 20: 3971
• 8i Wan J.-P, Tu Z, Wang Y. Chem. Eur. J. 2019; 25: 6907
• 8j Fu L, Wan J.-P. Asian J. Org. Chem. 2019; 8: 767
• 9 Joussot J, Schoenfelder A, Larquetoux L, Nicolas M, Suffert J, Blond G. Synthesis 2016; 48: 3364
• 10 Lin Y.-F, Fong C, Peng W.-L, Tang K.-C, Liang Y.-E, Li W.-T. J. Org. Chem. 2017; 82: 10855
• 11 Bagle PN, Mane MV, Sancheti SP, Gade AB, Shaikh SR, Baik M.-H, Patil NT. Org. Lett. 2019; 21: 335
• 12a Saniewski M, Horbowicz M, Kanlayanarat S. J. Hortic. Res. 2014; 22: 5
• 12b Wang H.-B, Wang X.-Y, Liu L.-P, Qin G.-W, Kang T.-G. Chem. Rev. 2015; 115: 2975
• 12c Guo H, Roman D, Beemelmanns C. Nat. Prod. Rep. 2019; 36: 1137
• 13a Allen JM, Lambert TH. J. Am. Chem. Soc. 2011; 133: 1260
• 13b Yunnikova LP, Akent’eva TA, Ésenbaeva VV. Pharm. Chem. J. 2015; 49: 243
• 13c Lyons DJ. M, Crocker RD, Blümel M, Nguyen TV. Angew. Chem. Int. Ed. 2017; 56: 1466; Angew. Chem. 2017, 129, 1488
• 13d Lyons DJ. M, Crocker RD, Nguyen TV. Chem. Eur. J. 2018; 24: 10959
• 13e Shao X, Tian L, Wang Y. Eur. J. Org. Chem. 2019; 2019: 4089
• 13f Mato M, García-Morales C, Echavarren AM. ChemCatChem 2019; 11: 53
• 14 Wen C, Yu G, Ou Y, Wang X, Zhang K, Chen Q. Tetrahedron Lett. 2019; 60: 1345
• 15a Cheng D, Wu L, Lv H, Xu X, Yan J. J. Org. Chem. 2017; 82: 1610
• 15b Cheng D, Chen T, Xu X, Yan J. Adv. Synth. Catal. 2018; 360: 901
• 15c Cheng D, Deng Z, Yan X, Wang M, Xu X, Yan J. Adv. Synth. Catal. 2019; 361: 5025
• 15d Cheng D, Wang M, Deng Z, Yan X, Xu X, Yan J. Eur. J. Org. Chem. 2019; 2019: 4589
• 15e Deng Z, Cheng D, Xu X, Yan J. Asian J. Org. Chem. 2019; 8: 283
• 15f Cheng D, Yan X, Shen J, Pu Y, Xu X, Yan J. Synthesis 2020; 52: 1833
• 16 Wendlandt AE, Stahl SS. Angew. Chem. Int. Ed. 2015; 54: 14638 ; Angew. Chem. 2015, 127, 14848
• 17a Gamill RB. Synthesis 1979; 901
• 17b Löwe W, Kietzmann A. Arch. Pharm. 1995; 328: 11
• 17c Hovey MT, Check CT, Sipher AF, Scheidt KA. Angew. Chem. Int. Ed. 2014; 53: 9603 ; Angew. Chem. 2014, 126, 9757