A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans

Anton S. Makarov; Anna E. Kekhvaeva; Petrakis N. Chalikidi; Vladimir T. Abaev; Igor V. Trushkov; Maxim G. Uchuskin

doi:10.1055/s-0039-1690000

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(19): 3747-3757
DOI: 10.1055/s-0039-1690000

paper

A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans

Autor*innen

Anton S. Makarov

^aPerm State University, Bukireva st. 15, 614990 Perm, Russian Federation eMail: mu@psu.ru
Anna E. Kekhvaeva

^aPerm State University, Bukireva st. 15, 614990 Perm, Russian Federation eMail: mu@psu.ru
Petrakis N. Chalikidi

^bK. L. Khetagurov North Ossetian State University, Vatutina st. 46, 362025 Vladikavkaz, Russian Federation
Vladimir T. Abaev

^bK. L. Khetagurov North Ossetian State University, Vatutina st. 46, 362025 Vladikavkaz, Russian Federation
Igor V. Trushkov

^cDmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela st. 1, 117997 Moscow, Russian Federation

^dN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation
Maxim G. Uchuskin ∗

^aPerm State University, Bukireva st. 15, 614990 Perm, Russian Federation eMail: mu@psu.ru

Abstract

Alle Artikel dieser Rubrik

Abstract

The Brönsted acid-catalyzed cascade synthesis of densely substituted benzofurans from easily available salicyl alcohols and biomass-derived furans has been developed. The disclosed sequence includes the intermediate formation of 2-(2-hydroxybenzyl)furans that quickly rearrange into functionalized benzofurans. The established protocol was applied for the total synthesis of sugikurojinol B.

Key words

furan - benzofuran - rearrangement - sugikurojinol B

Volltext

Referenzen

References

1a Goyal D, Kaur A, Goyal B. ChemMedChem 2018; 13: 1275
1b Heravi MM, Zadsirjan V, Hamidi H, Amiri PH. T. RSC Adv. 2017; 7: 24470
1c Nevagi RJ, Dighe SN, Dighe SN. Eur. J. Med. Chem. 2015; 97: 561
1d Khanam H. Shamsuzzaman Eur. J. Med. Chem. 2015; 97: 483
1e Hiremathad A, Patil MR, Chethana KR, Chand K, Santos MA, Keri RS. RSC Adv. 2015; 5: 96809

2 Bhalla S, Balasubramanian S, David K, Sirisawad M, Buggy J, Mauro L, Prachand S, Miller R, Gordon LI, Evens AM. Clin. Cancer Res. 2009; 15: 3354

3a Hughes ZA, Starr KR, Langmead CJ, Hill M, Bartoszyk GD, Hagan JJ, Middlemiss DN, Dawson LA. Eur. J. Pharmacol. 2005; 510: 49
3b Page ME, Cryan JF, Sullivan A, Dalvi A, Saucy B, Manning DR, Lucki I. J. Pharmacol. Exp. Ther. 2002; 302: 1220

4 Delini-Stula A, Fischbach R, Gnirss F, Bures E, Pöldinger W. Drug Dev. Res. 1985; 6: 371
5 Lotufo-Neto F, Trivedi M, Thase ME. Neuropsychopharmacology 1999; 20: 226
6 Hwang S.-K, Juhasz A, Yoon S.-H, Bodor N. J. Med. Chem. 2000; 43: 1525
7 Laina A, Karlis G, Liakos A, Georgiopoulos G, Oikonomou D, Kouskouni E, Chalkias A, Xanthos T. Int. J. Cardiol. 2016; 221: 780
8 Gautier P, Serre M, Cosnier-Pucheu S, Djandjighian L, Roccon A, Herbert J.-M, Nisato D. J. Cardiovasc. Pharmacol. 2005; 45: 125
9 Reichi S, Müller-Goymann CC. Int. J. Pharm. 2003; 250: 191
10 Halfpenny PR, Horwell DC, Hughes J, Hunter JC, Rees DC. J. Med. Chem. 1990; 33: 286
11 Rao GH, Pandey M, Narayanaswamy K, Rao RS, Pandey SS, Hayase S, Singh SP. ACS Omega 2018; 3: 13919
12 Sun Y.-Y, Liao J.-H, Fang J.-M, Chou P.-T, Shen C.-H, Hsu C.-W, Chen L.-C. Org. Lett. 2006; 8: 3713
13 Chen H, Delaunay W, Li J, Wang Z, Bouit P.-A, Tondelier D, Geffroy B, Mathey F, Duan Z, Reau R, Hissler M. Org. Lett. 2013; 15: 330

14a Galvani G, Harsha Vardhan Reddy K, Beauvineau C, Ghermani N, Mahuteau-Betzer F, Alami M, Messaoudi S. Org. Lett. 2017; 19: 910
14b Takahashi M, Nakano K, Nozaki K. J. Org. Chem. 2015; 80: 3790

15a Zhang L, Zhu L, Zhang Y, Yang Y, Wu Y, Ma W, Lan Y, You J. ACS Catal. 2018; 8: 8324
15b Yang K, Pulis AP, Perry GJ. P, Procter DJ. Org. Lett. 2018; 20: 7498
15c Payer SE, Pollak H, Schmidbauer B, Hamm F, Juricic F, Faber K, Glueck SM. Org. Lett. 2018; 20: 5139
15d Huang Z, Lumb J.-P. ACS Catal. 2019; 9: 521
15e Li G, Gao P, Lv X, Qu C, Yan Q, Wang Y, Yang S, Wang J. Org. Lett. 2017; 19: 2682
15f Chattopadhyay B, Dannatt JE, Andujar-De Sanctis IL, Gore KA, Maleczka RE. Jr, Singleton DA, Smith MR. J. Am. Chem. Soc. 2017; 139: 7864

16a Singh G, Goswami P, Sharma S, Anand RV. J. Org. Chem. 2018; 83: 10546
16b Srinivas K, Sharma R, Ramana CV. J. Org. Chem. 2017; 82: 9816
16c McComas CC, Palani A, Chang W, Holloway MK, Lesburg CA, Li P, Liverton N, Meinke PT, Olsen DB, Peng X, Soll RM, Ummat A, Wu J, Wu J, Zorn N, Ludmerer SW. ChemMedChem 2017; 12: 1436

17a Alonso-Maranon L, Martinez MM, Sarandeses LA, Gomez-Bengoa E, Perez Sestelo J. J. Org. Chem. 2018; 83: 7970
17b Yamaguchi M, Akiyama T, Sasou H, Katsumata H, Manabe K. J. Org. Chem. 2016; 81: 5450
17c Xia Z, Khaled O, Mouries-Mansuy V, Ollivier C, Fensterbank L. J. Org. Chem. 2016; 81: 7182

18a Du JY, Ma YH, Yuan RQ, Xin N, Nie SZ, Ma CL, Li CZ, Zhao CQ. Org. Lett. 2018; 20: 477
18b Rajesh M, Thirupathi N, Reddy TJ, Kanojiya S, Reddy MS. J. Org. Chem. 2015; 80: 12311
18c Fisher KM, Bolshan Y. J. Org. Chem. 2015; 80: 12676

19a Murai M, Okamoto K, Miki K, Ohe K. Tetrahedron 2015; 71: 4432
19b Skillinghaug B, Skold C, Rydfjord J, Svensson F, Behrends M, Savmarker J, Sjoberg PJ, Larhed M. J. Org. Chem. 2014; 79: 12018
19c Wang X, Liu M, Xu L, Wang Q, Chen J, Ding J, Wu H. J. Org. Chem. 2013; 78: 5273

20a Zhang Y, He Y, Li L, Ji M, Li XZ, Zhu G. J. Org. Chem. 2018; 83: 2898
20b Ha H.-J, Kang DW, Kim H.-M, Kang J.-M, Ann J, Hyun HJ, Lee JH, Kim SH, Kim H, Choi K, Hong H.-S, Kim Y, Jo D.-G, Lee J, Lee J. J. Med. Chem. 2018; 61: 396
20c Wang Z, Wang Y, Wang B, Li W, Huang L, Li X. J. Med. Chem. 2015; 58: 8616

21a Lin D, Wang L, Yan ZZ, Ye J, Hu AX, Liao HD, Liu J, Peng JM. RSC Adv. 2018; 8: 34331
21b Rehan M, Nallagonda R, Das BG, Meena T, Ghorai P. J. Org. Chem. 2017; 82: 3411
21c Li Y, Qiu D, Gu R, Wang J, Shi J, Li Y. J. Am. Chem. Soc. 2016; 138: 10814

22a Abaev VT, Trushkov IV, Uchuskin MG. Chem. Heterocycl. Compd. 2016; 52: 973
22b Trushkov IV, Uchuskin MG, Butin AV. Eur. J. Org. Chem. 2015; 2015: 2999
22c Peng H, Li J, Wang F, Liu B, Yin B. J. Org. Chem. 2016; 81: 4939
22d Yin B, Yu H, Li Z, Zhong W, Gub W. Synthesis 2012; 44: 3735
22e Yu H, Zhong W, He T, Gu W, Yin B. Tetrahedron Lett. 2013; 54: 1256

23 Kuznetsov A, Makarov A, Rubtsov AE, Butin AV, Gevorgyan V. J. Org. Chem. 2013; 78: 12144

24a Makarov AS, Kekhvaeva AE, Hall CJ. J, Price DR, Trushkov IV, Uchuskin MG. Tetrahedron 2017; 73: 7042
24b Gutnov AV, Butin AV, Abaev VT, Krapivin GD, Zavodnik VE. Molecules 1999; 4: 204

25a Li T.-Z, Geng C.-A, Yin X.-J, Yang T.-H, Chen X.-L, Huang X.-Y, Ma Y.-B, Zhang X.-M, Chen J.-J. Org. Lett. 2017; 19: 429
25b Zhang Y, Guo Y, Li Z, Xie Z. Org. Lett. 2016; 18: 4578
25c Xu L, Liu F, Xu LW, Gao Z, Zhao YM. Org. Lett. 2016; 18: 3698

26a Lee JE, Kwon TH, Gu SJ, Lee DH, Kim BM, Lee JY, Lee JK, Seo SH, Pae AN, Keum G, Cho YS, Min SJ. Org. Biomol. Chem. 2014; 12: 5669
26b Tapia R, Guardia JJ, Alvarez E, Haidour A, Ramos JM, Alvarez-Manzaneda R, Chahboun R, Alvarez-Manzaneda E. J. Org. Chem. 2012; 77: 573

27 Aoyama T, Yamamoto T, Miyota S, Hayakawa M, Takido T, Kodomari M. Synlett 2014; 25: 1571
28 Arihara S, Umeyama A, Bando S, Imoto S, Ono M, Yoshikawa K. Chem. Pharm. Bull. 2004; 52: 463

29a Monzon DM, Santos T, Pinacho-Crisostomo F, Martin VS, Carrillo R. Chem. Asian J. 2018; 13: 325
29b Merkushev AA, Strel’nikov VN, Uchuskin MG, Trushkov IV. Tetrahedron 2017; 73: 6523
29c Butin AV, Nevolina TA, Shcherbinin VA, Uchuskin MG, Serdyuk OV, Trushkov IV. Synthesis 2010; 2969

30a Aoyama T, Furukawa T, Hayakawa M, Takido T, Kodomari M. Synlett 2015; 26: 1875
30b Li Z, Shi Z, He C. J. Organomet. Chem. 2005; 690: 5049

31 Wu SY, Hirashima A, Kuwano E, Eto M. Agric. Biol. Chem. 1987; 51: 537
32 Katritzky AR, Ji Y, Fang Y, Prakash I. J. Org. Chem. 2001; 66: 5613
33 Alaimo PJ, Knight ZA, Shokat KM. Bioorg. Med. Chem. 2005; 13: 2825

Zusatzmaterial

Supporting Information (PDF) (opens in new window)