Efficient Synthesis of Chromenes from Vinyl o-Quinone Methides via a Brønsted Acid Catalyzed Electrocyclization Process

Abstract

An efficient approach for the synthesis of chromene derivatives from vinyl o-quinone methides was established via a Brønsted acid catalyzed electrocyclization. By using this methodology, a series of structurally diversified chromenes was synthesized in a highly atom-economic and environmentally benign manner with generally good to excellent yields (up to 98% yield). This reaction will not only provide an efficient method for the construction of chromene scaffolds, but also enrich the research area of o-quinone methides.

Key words

o-quinone methide - electrocyclization - Brønsted acid catalysis - chromenes - heterocycles

• References

• 1 These authors contributed equally to this work.

For selected reviews, see:
• 2a Pratap R. Ram VJ. Chem. Rev. 2014; 114: 10476
• 2b Costa M. Dias TA. Brito A. Proenca F. Eur. J. Med. Chem. 2016; 123: 487
• 3a Cheenpracha S. Karalai C. Ponglimanont C. Kanjana-Opas A. J. Nat. Prod. 2009; 72: 1395
• 3b Chen J. Leng H. Duan Y. Zhao W. Yang G. Guo Y. Chen Y. Hu Q. Phytochem. Lett. 2013; 6: 144
• 4 Liby K. Rendi M. Suh N. Royce DB. Risingsong R. Williams CR. Lamph W. Labrie F. Krajewski S. Xu X. Kim H. Brown P. Sporn MB. Clin. Cancer Res. 2006; 12: 5902
• 5 Cheng J.-F. Ishikawa A. Ono Y. Arrhenius T. Nadzan A. Bioorg. Med. Chem. Lett. 2003; 13: 3647
• 6 Chen B. Fairhurst RA. Floersheimer A. Furet P. Jiang S. Lu W. Marsilje TH. Vaupel A. Patent WO2011064211A1, 2011

For selected reviews, see:
• 7a Shi Y.-L. Shi M. Org. Biomol. Chem. 2007; 5: 1499
• 7b Ferreira SB. da Silva F. dC. Pinto AC. Gonzaga DT. G. Ferreira VF. J. Heterocycl. Chem. 2009; 46: 1080
• 7c Majumdar N. Paul ND. Mandal S. de Bruin B. Wulff WD. ACS Catal. 2015; 5: 2329
• 7d Sadek KU. Mekheimer RA. H. Abd-Elmonem M. Abdel-Hameed A. Elnagdi MH. Tetrahedron 2017; 28: 1462

For selected examples, see:
• 8a Wang Z.-Q. Lei Y. Zhou M.-B. Chen G.-X. Song R.-J. Xie Y.-X. Li J.-H. Org. Lett. 2011; 13: 14
• 8b Cui Z. Shang X. Shao X.-F. Liu Z.-Q. Chem. Sci. 2012; 3: 2853
• 8c Hornillos V. van Zijl AW. Feringa BL. Chem. Commun. 2012; 48: 3712
• 8d Majumdar N. Korthals KA. Wulff WD. J. Am. Chem. Soc. 2012; 134: 1357
• 8e Paul ND. Mandal S. Otte M. Cui X. Zhang XP. de Bruin B. J. Am. Chem. Soc. 2014; 136: 1090
• 8f Siyang H.-X. Wu X.-R. Ji X.-Y. Wu X.-Y. Liu P.-N. Chem. Commun. 2014; 50: 8514
• 8g Zeng B.-S. Yu X.-Y. Siu P.-W. Scheidt KA. Chem. Sci. 2014; 5: 2277
• 8h Wang P.-S. Liu P. Zhai Y.-J. Lin H.-C. Han Z.-Y. Gong L.-Z. J. Am. Chem. Soc. 2015; 137: 12732
• 8i Kuppusamy R. Muralirajan K. Cheng C.-H. ACS Catal. 2016; 6: 3909
• 8j Qiu Y.-F. Song X.-R. Li M. Zhu X.-Y. Wang A.-Q. Yang F. Han Y.-P. Zhang H.-R. Jin D.-P. Li Y.-X. Liang Y.-M. Org. Lett. 2016; 18: 1514
• 8k Liu S. Chen K. Lan X.-C. Hao W.-J. Li G. Tu S.-J. Jiang B. Chem. Commun. 2017; 53: 10692
• 8l Xia J. Nie Y. Yang G. Liu Y. Zhang W. Org. Lett. 2017; 19: 4884
• 8m Zheng Y. Qiu L. Hong K. Dong S. Xu X. Chem. Eur. J. 2018; DOI 10.1002/chem.201704759
• 8n Ma C. Zhao Y. Org. Biomol. Chem. 2018; 16: 703

For related reviews, see:
• 9a Akiyama T. Chem. Rev. 2007; 107: 5744
• 9b Parmar D. Sugiono E. Raja S. Rueping M. Chem. Rev. 2014; 114: 9047
• 9c Terada M. Chem. Commun. 2008; 4097
• 9d Terada M. Synthesis 2010; 1929
• 9e Yu J. Shi F. Gong L.-Z. Acc. Chem. Res. 2011; 44: 1156

For some examples, see:
• 10a Gharpure SJ. Sathiyanarayanan AM. Vuram PK. RSC Adv. 2013; 3: 18279
• 10b Hsiao C.-C. Raja S. Liao H.-H. Atodiresei I. Rueping M. Angew. Chem. Int. Ed. 2015; 54: 5762
• 10c Zhao J.-J. Sun S.-B. He S.-H. Wu Q. Shi F. Angew. Chem. Int. Ed. 2015; 54: 5460

For related reviews, see:
• 11a Pathak TP. Sigman MS. J. Org. Chem. 2011; 76: 9210
• 11b Willis NJ. Bray CD. Chem. Eur. J. 2012; 18: 9160
• 11c Bai W.-J. David JG. Feng Z.-G. Weaver MG. Wu K.-L. Pettus TR. R. Acc. Chem. Res. 2014; 47: 3655
• 11d Singh MS. Nagaraju A. Anand N. Chowdhury S. RSC Adv. 2014; 4: 55924
• 11e Wang Z. Sun J. Synthesis 2015; 47: 3629
• 11f Jaworski AA. Scheidt KA. J. Org. Chem. 2016; 81: 10145

For selected 1,4-additions of o-QMs, see:
• 12a Mattson AE. Scheidt KA. J. Am. Chem. Soc. 2007; 129: 4508
• 12b Luan Y. Schaus SE. J. Am. Chem. Soc. 2012; 134: 19965
• 12c Guo WG. Wu B. Zhou X. Chen P. Wang X. Zhou YG. Liu Y. Li C. Angew. Chem. Int. Ed. 2015; 54: 4522
• 12d Lewis RS. Garza CJ. Dang AT. Pedro TK. A. Chain WJ. Org. Lett. 2015; 17: 2278
• 12e Zhao W. Wang Z. Chu B. Sun J. Angew. Chem. Int. Ed. 2015; 54: 1910
• 12f Wang Z. Ai F. Wang Z. Zhao W. Zhu G. Lin Z. Sun J. J. Am. Chem. Soc. 2015; 137: 383

For [4+1] annulations of o-QMs, see:
• 13a Jiang X.-L. Liu S.-J. Gu Y.-Q. Mei G.-J. Shi F. Adv. Synth. Catal. 2017; 359: 3341
• 13b Lian X.-L. Adili A. Liu B. Tao Z.-L. Han Z.-Y. Org. Biomol. Chem. 2017; 15: 3670
• 13c Yang Q.-Q. Xiao W.-J. Eur. J. Org. Chem. 2017; 233

For selected [4+2] annulations of o-QMs, see:
• 14a Saha S. Schneider C. Org. Lett. 2015; 17: 648
• 14b Yu X.-Y. Chen J.-R. Wei Q. Cheng H.-G. Liu Z.-C. Xiao W.-J. Chem. Eur. J. 2016; 22: 6774
• 14c Zhang Y.-C. Zhu Q.-N. Yang X. Zhou L.-J. Shi F. J. Org. Chem. 2016; 81: 1681
• 14d Chen P. Wang K. Guo W. Liu X. Liu Y. Li C. Angew. Chem. Int. Ed. 2017; 56: 3689
• 14e Wang Z. Sun J. Org. Lett. 2017; 19: 2334

For [4+3] annulations of o-QMs, see:
• 15a Izquierdo J. Orue A. Scheidt KA. J. Am. Chem. Soc. 2013; 135: 10634
• 15b Lv H. Jia WQ. Sun L.-H. Ye S. Angew. Chem. Int. Ed. 2013; 52: 8607
• 15c Mei G.-J. Zhu Z.-Q. Zhao J.-J. Bian C.-Y. Chen J. Chen R.-W. Shi F. Chem. Commun. 2017; 53: 2768

For selected examples of o-VQMs-involved reactions, see:
• 16a Lv H. You L. Ye S. Adv. Synth. Catal. 2009; 351: 2822
• 16b Adili A. Tao Z.-L. Chen D.-F. Han Z.-Y. Org. Biomol. Chem. 2015; 13: 2247
• 16c Ref. 10b
• 16d Jin J.-H. Li X.-Y. Luo X. Fossey JS. Deng W.-P. J. Org. Chem. 2017; 82: 5424
• 16e Wang Z. Wang T. Yao W. Lu Y. Org. Lett. 2017; 19: 4126
• 17a For an early example, see: Jurd L. Tetrahedron 1977; 33: 163
• 17b For a mechanistic investigation, see: Bishop LM. Winkler M. Houk KN. Bergman RG. Trauner D. Chem. Eur. J. 2008; 14: 5405
• 17c For a catalytic asymmetric transformation, see: Rueping M. Uria U. Lin M.-Y. Atodiresei I. J. Am. Chem. Soc. 2011; 133: 3732