Efficient Synthesis of Benzospirocyclohexadienones via PIFA-Promoted Intramolecular Dearomative Spiroannulation

Abstract

A rapid and convenient method for the synthesis of differently substituted spiro[cyclohexane-1,1′-isochromane]-2,5-dien-4-one derivatives via phenyliodine(III) bis(trifluoroacetate) (PIFA)-promoted intramolecular oxidative dearomatization at the para position is disclosed, with the aim of building a library of new spirocyclohexadienone scaffolds. Subsequently, this strategy is modified to access novel cyclohexanedienone-containing polycyclic compounds.

Key words

spirocyclic compounds - cyclohexadienones - hypervalent iodine(III) reagents - phenyliodine(III) bis(trifluoroacetate) - dearomatization

Publication History

Received: 09 August 2024

Accepted after revision: 07 October 2024

Article published online:
22 October 2024

• References

• 1 Moshnenko N, Kazantsev A, Chupakhin E, Bakulina O, Dar’in D. Molecules 2023; 28: 4209
• 2 Altei WF, Pachane BC, Martins LJ, Gomes RC, Santos RN, Fernandes DC, Selistre-de-Araújo HS, Coelho F, Andricopulo AD. Anti-Cancer Agents Med. Chem. 2021; 21: 1901
• 3 Chen C, He L. Eur. J. Med. Chem. 2020; 203: 112577
• 4 Park HB, Kim Y.-J, Lee JK, Lee KR, Kwon HC. Org. Lett. 2012; 14: 5002
• 5 Xu K, Jiang J.-S, Feng Z.-M, Yang Y.-N, Li L, Zang C.-X, Zhang P.-C. J. Nat. Prod. 2016; 79: 1567
• 6 Fu J.-J, Qin J.-J, Zeng Q, Huang Y, Jin HZ, Zhang W.-D. Chem. Pharm. Bull. 2010; 58: 1263
• 7 Kováčová S, Adla SK, Maier L, Babiak M, Mizushina Y, Paruch K. Tetrahedron 2015; 71: 7575
• 8 Al-Tel TH, Srinivasulu V, Ramanathan M, Soares NC, Sebastian A, Bolognesi ML, Abu-Yousef IA, Majdalawieh A. Org. Biomol. Chem. 2020; 18: 8526
• 9 Yang J, Wang Y, Guan W, Su W, Li G, Zhang S, Yao H. Eur. J. Med. Chem. 2022; 237: 114361
• 10 Hiesinger K, Dar’in D, Proschak E, Krasavin M. J. Med. Chem. 2021; 64: 150
• 11 Wang L, Yang Z, Ni T, Shi W, Guo Y, Li K, Shi A, Wu S, Sheng C. Bioorg. Med. Chem. Lett. 2020; 30: 126662
• 12 Gomes CR, Sakata PR, Almeida PW, Coelho F. Med. Chem. 2019; 15: 373
• 13 Forren MJ, Roberts CA, Allen ST, Helmy S. Dyes Pigm. 2021; 194: 109619
• 14 Omolo JJ, Johnson MM, van Vuuren SF, de Koning CB. Bioorg. Med. Chem. Lett. 2011; 21: 7085
• 15 Mizushina Y, Maeda N, Kuriyama I, Yoshida H. Expert. Opin. Invest. Drugs 2011; 20: 1523
• 16 Mizushina Y, Kamisuki S, Mizuno T, Takemura M, Asahara H, Linn S, Yamaguchi T, Matsukage A, Hanaoka F, Yoshida S, Saneyoshi M, Sugawara F, Sakaguchi K. J. Biol. Chem. 2000; 275: 33957
• 17 Blizzard TA, DiNinno F, Chen HY, Kim S, Wu JY, Chan W, Birzin ET, Yang YT, Pai L.-Y, Hayes EC, DaSilva CA, Rohrer SP, Schaeffer JM, Hammond ML. Bioorg. Med. Chem. Lett. 2005; 15: 3912
• 18 Grese TA, Pennington LD, Sluka JP, Adrian MD, Cole HW, Fuson TR, Magee DE, Phillips DL, Rowley ER, Shetler PK, Short LL, Venugopalan M, Yang NN, Sato M, Glasebrook AL, Bryant HU. J. Med. Chem. 1998; 41: 1272
• 19 Zhang Z, Chen Q, Li Y, Doss GA, Dean BJ, Ngui JS, Silva Elipe M, Kim S, Wu JY, DiNinno F, Hammond ML, Stearns RA, Evans DC, Baillie TA, Tang W. Chem. Res. Toxicol. 2005; 18: 675
• 20 Stern AJ, Swenton JS. J. Org. Chem. 1988; 53: 2465
• 21 Venkateswarlu R, Kamakshi C, Moinuddin SG. A, Subhash PV, Ward RS, Pelter A, Coles SJ, Hursthouse MB, Light ME. Tetrahedron 2001; 57: 5625
• 22 Kim S, Wu JY, Zhang Z, Tang W, Doss GA, Dean BJ, DiNinno F, Hammond ML. Org. Lett. 2005; 7: 411
• 23 Dohi T, Maruyama A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer SB, Kita Y. Angew. Chem. Int. Ed. 2008; 47: 3787
• 24 Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2010; 49: 2175
• 25 Uyanik M, Yasui T, Ishihara K. Tetrahedron 2010; 66: 5841
• 26 Uyanik M, Yasui T, Ishihara K. Angew. Chem. Int. Ed. 2013; 52: 9215
• 27 Dohi T, Takenaga N, Nakae T, Toyoda Y, Yamasaki M, Shiro M, Fujioka H, Maruyama A, Kita Y. J. Am. Chem. Soc. 2013; 135: 4558
• 28 Zheng H, Sang Y, Houk KN, Xue X.-S, Cheng J.-P. J. Am. Chem. Soc. 2019; 141: 16046
• 29 Dohi T, Sasa H, Miyazaki K, Fujitake M, Takenaga N, Kita Y. J. Org. Chem. 2017; 82: 11954
• 30 Ogasawara M, Sasa H, Hu H, Amano Y, Nakajima H, Takenaga N, Nakajima K, Kita Y, Takahashi T, Dohi T. Org. Lett. 2017; 19: 4102
• 31 Hempel C, Maichle-Mössmer C, Pericàs MA, Nachtsheim BJ. Adv. Synth. Catal. 2017; 359: 2931
• 32 Uyanik M, Yasui T, Ishihara K. J. Org. Chem. 2017; 82: 11946
• 33 Abazid AH, Nachtsheim BJ. Angew. Chem. Int. Ed. 2020; 59: 1479
• 34 Wang Y, Zhao C.-Y, Wang Y.-P, Zheng W.-H. Synthesis 2019; 51: 3675
• 35 Paladino M, Zaifman J, Ciufolini MA. Org. Lett. 2015; 17: 3422
• 36 Canesi S, Bouchu D, Ciufolini MA. Angew. Chem. Int. Ed. 2004; 43: 4336
• 37 Rocq C, Denis M, Canesi S. Chem. Commun. 2023; 59: 6495
• 38 Uyanik M, Sasakura N, Mizuno M, Ishihara K. ACS Catal. 2017; 7: 872
• 39 Suzuki T, Watanabe S, Uyanik M, Ishihara K, Kobayashi S, Tanino K. Org. Lett. 2018; 20: 3919
• 40 Jain N, Hein JE, Ciufolini MA. Synlett 2019; 30: 1222
• 41 Jain N, Xu S, Ciufolini MA. Chem. Eur. J. 2017; 23: 4542
• 42 Siddiqi Z, Bingham TW, Shimakawa T, Hesp KD, Shavnya A, Sarlah D. J. Am. Chem. Soc. 2024; 146: 2358
• 43 Kumar R, Singh FV, Takenaga N, Dohi T. Chem. Asian J. 2022; 17: e202101115
• 44 Singh FV, Kole PB, Mangaonkar SR, Shetgaonkar SE. Beilstein J. Org. Chem. 2018; 14: 1778
• 45 Harned AM. Tetrahedron Lett. 2014; 55: 4681
• 46 Kondratov IS, Tolmachova NA, Haufe G. Eur. J. Org. Chem. 2018; 3618