Base-Catalyzed Synthesis of Flavones via Thiol-Assisted Sequential Demethylation/Cyclization of 1-(2-Methoxyphenyl)prop-2-yn-1-ones

Ritiele Heck; Thiago Anjos; Maira R. Giehl; Ricardo F. Schumacher; Benhur Godoi

doi:10.1055/a-1874-5283

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(20): 4601-4607
DOI: 10.1055/a-1874-5283

paper

Base-Catalyzed Synthesis of Flavones via Thiol-Assisted Sequential Demethylation/Cyclization of 1-(2-Methoxyphenyl)prop-2-yn-1-ones

Ritiele Heck

^aPrograma de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, Cerro Largo, RS, Brazil

,

Thiago Anjos

^bDepartment of Chemistry, Federal University of Santa Maria-UFSM, 97105-900, Santa Maria, RS, Brazil

,

Maira R. Giehl

^aPrograma de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, Cerro Largo, RS, Brazil

,

Ricardo F. Schumacher

^bDepartment of Chemistry, Federal University of Santa Maria-UFSM, 97105-900, Santa Maria, RS, Brazil

,

Benhur Godoi ∗

^aPrograma de Pós-Graduação em Ambiente e Tecnologias Sustentáveis, Núcleo de Síntese, Aplicação e Análise de Compostos Orgânicos e Inorgânicos, Federal University of Fronteira Sul, Cerro Largo, RS, Brazil

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Flavone and analogues represent an important class of biologically and pharmacologically active substances commonly found in the composition of diverse plants as part of the class of secondary metabolites. Herein, an efficient and regioselective synthetic strategy for the preparation of functionalized flavones is demonstrated through sequential demethylation/6-endo-dig intramolecular cyclization of propyn-1-ones, using catalytic amounts of base in the presence of a thiol, by employing NMP as the solvent. The reactions proceeded smoothly under transition-metal-free and open to air conditions, furnishing the desired six-membered heterocycles in moderate to excellent yields, in short reaction time.

Key words

flavones - demethylation - cyclization - base-catalysis - thiols

Volltext

Referenzen

References

1a Alsharairi NA. Int. J. Environ. Res. Public Health 2021; 18: 5243
1b Olennikov DN, Chirikova NK. Chem. Nat. Compd. 2021; 57: 436
1c Albouchi F, Avola R, Dico GM. L, Calabrese V, Graziano AC. E, Abderrabba M, Cardile V. Molecules 2018; 23: 2526

2 Nijveldt R, Nood EV, Hoorn DE. C. V, Boelens PG, Norren KV, Leeuwen PA. M. V. Am. J. Clin. Nutr. 2001; 74: 418

3a Reis J, Gaspar A, Milhazes N, Borges F. J. Med. Chem. 2017; 60: 7941
3b Singh M, Kaur M, Silakari O. Eur. J. Med. Chem. 2014; 84: 206

4 Reséndiz MF, Oliveras PL, Rubalcava ML. M. Appl. Microbiol. Biotechnol. 2021; 105: 4225
5 Chumkaew P, Srisawat T. Chem. Nat. Compd. 2021; 57: 274
6 Abo-Salem HM, Gibriel AA, El Awady ME, Mandour AH. Med. Chem. 2021; 17: 158
7 Hida T, Tamiya M, Nishio M, Yamamoto N, Hirashima T, Horai T, Tanii H, Shi MM, Kobayashi K, Horio Y. Cancer Sci. 2011; 102: 845
8 Wang B, Qu J, Luo S, Feng S, Li T, Yuan M, Huang Y, Liao J, Yang R, Ding C. Molecules 2018; 23: 2513
9 Wu X, Song M, Gao Z, Sun Y, Wang M, Li F, Zheng J, Xiao H. J. Nutr. Biochem. 2017; 42: 17

10a Chang M.-Y, Tsai M.-C, Lin C.-Y. RSC Adv. 2021; 11: 11655
10b Kshatriya R, Jejurkar VP, Saha S. Tetrahedron 2018; 74: 811
10c Santos CM. M, Silva AM. S. Eur. J. Org. Chem. 2017; 3115

11a Vimal M, Pathak U, Halve AK. Synth. Commun. 2019; 49: 2805
11b Liu R, Zhang Y, Xu K, Tan G. Synth. Commun. 2017; 47: 1

12a McGarry LW, Detty MR. J. Org. Chem. 1990; 55: 4349
12b Nakatani K, Okamoto A, Saito I. Tetrahedron 1996; 52: 9421
12c Yoshida M, Fujino Y, Doi T. Org. Lett. 2011; 13: 4526

13a Zhao J, Zhao Y, Fu H. Org. Lett. 2012; 14: 2710
13b Zhao J, Zhao Y, Fu H. Angew. Chem. Int. Ed. 2011; 50: 3769

14a Sun D.-W, Zhou Y.-Y, Jiang M, Nian T, Liu J.-T. Tetrahedron 2021; 91: 132226
14b Son SH, Jang HJ, Cho YY, Kim DH, Yoo H.-S, Shin J.-W, Lee SJ, Kim YM, Kim N.-J. RSC Adv. 2021; 11: 14000
14c Godoi B, Sperança A, Menezes PH, Bruning CA, Nogueira CW, Back DF, Zeni G. Adv. Synth. Catal. 2011; 353: 2042
14d Zhou C, Dubrovsky AV, Larock RC. J. Org. Chem. 2006; 71: 1626

15a Patil AM, Kamble DA, Lokhande PD. Synth. Commun. 2018; 48: 1299
15b Gobbi S, Rampa A, Bisi A, Belluti F, Piazzi L, Valent P, Caputo A, Zampiron A, Carrara M. J. Med. Chem. 2003; 46: 3662
15c de la Torre MD. L, Marcorin GL, Pirri G, Tome AC, Silva AM. S, Cavaleira JA. S. Tetrahedron Lett. 2002; 43: 1689

16 Chakraborti AK, Sharma L, Nayak MK. J. Org. Chem. 2002; 67: 6406
17 Chow ST, Ng TL. Water Res. 1983; 17: 117
18 Nayak MK, Chakraborti AK. Tetrahedron Lett. 1997; 38: 8749

Zusatzmaterial

Supporting Information