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Synthesis 2023; 55(20): 3364-3372
DOI: 10.1055/a-2147-2620
DOI: 10.1055/a-2147-2620
paper
Rhodium-Catalyzed C–H Activation of 2-Arylquinazolinones and Cyclization with Elemental Sulfur via C–S/S–N Bond Formation to Access 7H-Benzo[4,5]isothiazolo[3,2-b]quinazolinones
Financial support from National Natural Science Foundation of China (no. 21762020 and 22261027) is gratefully acknowledged.
Abstract
An efficient method for the synthesis of 7H-benzo[4,5]isothiazolo[3,2-b]quinazolin-7-ones by the reaction of 2-arylquinazolin-4(3H)-ones and elemental sulfur is described. The rhodium-catalyzed C–H activation of 2-arylquinazolinones and cyclization with elemental sulfur via one-step formation of C–S/N–S bonds to give the corresponding 7H-benzo[4,5]isothiazolo[3,2-b]quinazolinones is realized in good to high yields with good functional group tolerance.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2147-2620.
- Supporting Information
Publication History
Received: 29 May 2023
Accepted after revision: 02 August 2023
Accepted Manuscript online:
02 August 2023
Article published online:
07 September 2023
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References
- 1a Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5
- 1b Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
- 1c Smith BR, Eastman M, Njardarson JT. J. Med. Chem. 2014; 57: 9764
- 2a Zhang JP, Zhang YB, Lin JB, Chen XM. Chem. Rev. 2012; 112: 1001
- 2b Craine L, Raban M. Chem. Rev. 1989; 89: 689
- 2c Fontana G. Curr. Bioact. Compd. 2010; 6: 284
- 2d Bradshaw TD, Wrigley S, Shi DF, Schultz RJ, Paull KD, Stevens MF. G. Br. J. Cancer 1998; 77: 745
- 2e Mortimer CG, Wells G, Crochard JP, Stone EL, Bradshaw TD, Stevens MF. G, Westwell AD. J. Med. Chem. 2006; 49: 179
- 2f Tekiner-Gulbas B, Temiz-Arpaci O, Yildiz I, Altanlar N. Eur. J. Med. Chem. 2007; 42: 1293
- 2g Keri RS, Patil MR, Patil SA, Bugagumpi S. Eur. J. Med. Chem. 2015; 89: 207
- 3a Novick RM, Nelson ML, Unice KM, Keenan JJ, Paustenbach DJ. Food Chem. Toxicol. 2013; 56: 60
- 3b Dahlin J, Isaksson M. Contact Dermatitis 2015; 73: 60
- 4a Younce JR, Davis AA, Black KJ. J. Parkinsons Dis. 2018; 9: 63
- 4b Shirley M. Drugs Ther. Perspect. 2021; 37: 347
- 4c Riva MA, Albert U, De Filippis S, Vita A, Berardis DDe. Ther. Adv. Psychopharmacol. 2021; 11: 1
- 4d Gan Z, Zhang M, Han H, Zhu Q, Li K. Bipolar Disord. 2020; 22: 425
- 4e Haranishi Y, Hara K, Terada T. Pharmacol. Biochem. Behav. 2020; 195: 172964
- 5a Silva AD. O, McQuade J, Szostak M. Adv. Synth. Catal. 2019; 361: 2050
- 5b Li T, Yang L, Ni KD, Shi ZY, Li F, Chen DY. Org. Biomol. Chem. 2016; 14: 6297
- 6a Bhakuni BS, Balkrishna SJ, Kumar A, Kumar S. Tetrahedron Lett. 2012; 53: 1354
- 6b Krasikova V, Katkevics M. Chem. Heterocycl. Comp. 2013; 48: 1684
- 6c Xie H, Li G, Zhang F, Xiao F, Deng GJ. Green Chem. 2018; 20: 827
- 7a Chen FJ, Liao G, Li X, Wu J, Shi BF. Org. Lett. 2014; 16: 5644
- 7b Guo JR, Gong JF, Song MP. Org. Biomol. Chem. 2019; 17: 5029
- 8 Moon S, Nishii Y, Miura M. Org. Lett. 2021; 23: 49
- 9 Tausch E, Ljungström V, Agathangelidis A, Zapatka M, Scarfò L, Jebaraj BM. C, Yosifov DY, Müller A, Munugalavadla V, Degenhardt JD, Ghia P, Rosenquist R, Stilgenbauer S. Blood 2022; 139: 3340
- 10a He D, Wang ML, Zhao SY, Shu YS, Zeng HL, Xiao C, Lu C, Liu YY. Fitoterapia 2017; 119: 136
- 10b Kshirsagar UA. Org. Biomol. Chem. 2015; 36: 9336
- 10c Micheal JP. Nat. Prod. Rep. 2008; 25: 166
- 10d Michael JP. Nat. Prod. Rep. 2007; 24: 223
- 10e Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
- 10f Michael JP. Nat. Prod. Rep. 2000; 17: 603
- 11a Gatadi S, Lakshmi TV, Nanduri S. Eur. J. Med. Chem. 2019; 170: 157
- 11b Hameed A, Al-Rashida M, Uroos M, Ali SA, Arshia, Ishtiaq M, Khan KM. Expert Opin. Ther. Pat. 2018; 28: 281
- 11c Ghorab MM, Alqahtani AS, Soliman AM, Askar AA. Int. J. Nanomed. 2020; 15: 3161
- 11d Soliman AM, Karam HM, Mekkawy MH, Ghorab MM. Eur. J. Med. Chem. 2020; 197: 112333
- 12a Plescia F, Maggio B, Daidone G, Raffa D. Eur. J. Med. Chem. 2021; 213: 113070
- 12b Auti PS, George G, Paul AT. RSC Adv. 2020; 10: 41353
-
12c
Xing ZM,
Wu WH,
Miao YX,
Tang YQ,
Zhou YK,
Zheng LF,
Song ZB,
Peng YY.
Org. Chem. Front. 2021; 8: 1867
- 12d Mohammadkhani L, Heravi MM. Front. Chem. 2020; 8: 580086
- 12e Ghosh P, Gangulya B, Das S. Org. Biomol. Chem. 2020; 18: 4497
- 12f Reddy MM, Sivaramakrishna A. J. Heterocycl. Chem. 2019; 57: 942
- 13a Liu HL, Li XT, Tian HZ, Sun XW. Org. Lett. 2021; 23: 4579
- 13b Alafeefy AM, Ashour AE, Prasad O, Sinha L, Pathak S, Alasmari FA, Rishi AK, Abdel-Aziz HA. Eur. J. Med. Chem. 2015; 92: 191
- 14 Wu Q, Deng ZH, Xie DY, Liu Y, Yang Q, Fu Y, Peng YY. Tetrahedron 2022; 124: 132911
- 15a Kang SD, Li JX, Yang Q, Song ZB, Peng YY. Eur. J. Org. Chem. 2022; e202200472
- 15b Huang J, Chen W, Liang JZ, Yang Q, Deng ZH, Song ZB, Peng YY. Org. Chem. Front. 2021; 8: 6837
- 15c Wang N, Yang Q, Deng ZH, Mao XC, Peng YY. ACS Omega 2020; 14635
- 15d Lou MH, Deng ZH, Mao XC, Fu Y, Yang Q, Peng YY. Org. Biomol. Chem. 2018; 16: 1851
- 15e Zhang YG, Huang J, Deng ZH, Mao XC, Peng YY. Tetrahedron 2018; 74: 2330
- 15f Jiang X, Yang Q, Yuan JJ, Deng ZH, Mao XC, Peng YY, Yu CY. Tetrahedron 2016; 72: 1238
For recent reviews, see:
For excellent reports, see:
For reviews, see:
For recent reviews on the biological activities of quinazolinone, see:
For selective recent reports, see:
For recent reviews, see:
For selected recent reports, see: