Tandem Oxidative Reaction of 1,3-Diarylpropenes and 5-Aminopyrazoles

Dongping Cheng; Huafang Gu; Hongshuang Xia; Yawei Wang; Jing-Hua Li; Xiaoliang Xu

doi:10.1055/a-2145-5916

Synlett, Table of Contents

Synlett 2023; 34(19): 2309-2314
DOI: 10.1055/a-2145-5916

letter

Tandem Oxidative Reaction of 1,3-Diarylpropenes and 5-Aminopyrazoles

Dongping Cheng∗

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Huafang Gu

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Hongshuang Xia

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Yawei Wang

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Jing-Hua Li∗

^aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

,

Xiaoliang Xu∗

^bCollege of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

The reaction of 5-aminopyrazoles with 1,3-diarylpropenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, with subsequent intramolecular cyclization and dehydroaromatization in the presence of Cu(OTf)₂/tert-butyl hydroperoxide, gave a series of pyrazolo[3,4-b]pyridines in moderate to excellent yields. The reaction has the advantages of high atom economy, a wide substrate scope, and a one-pot procedure.

Key words

oxidative coupling - tandem reaction - one-pot reaction - aminopyrazoles - diarylpropenes - pyrazolopyridines

Full Text

References

References and Notes

For representative examples, see:

1a Dodiya DK, Trivedi AR, Kataria VB, Shah VH. Curr. Org. Chem. 2012; 16: 400
1b Hu L, Li L, Chang Q, Fu S, Li Q. J. Med. Chem. 2020; 63: 11215
1c Abdel-latif E, Abdel-fattah S, Gaffer HE, Etman HA. Egypt. J. Basic Appl. Sci. 2016; 3: 118
1d Aly AA, El-Emary TI, Mourad A.-FE, Khallaf Alyan Z, Bräse S, Nieger M. J. Chem. Res. 2019; 43: 219
1e Donaire-Arias A, Montagut AM, Puig de la Bellacasa R, Estrada-Tejedor R, Teixidó J, Borrell JI. Molecules 2022; 27: 2237
1f Ji Y, Li L, Zhu G, Zhou Y, Lu X, He W, Gao L, Rong L. J. Heterocycl. Chem. 2020; 57: 1781
1g Liu N, Wang X, Fu Q, Qin Q, Wu T, Lv R, Zhao D, Cheng M. RSC Med. Chem. 2023; 14: 85
1h Mohamed MS, El-Deen Awad YS, El-Hallouty SM, El-Araby M. Open J. Med. Chem. 2012; 2: 78
1i Zhao B, Li Y, Xu P, Dai Y, Luo C, Sun Y, Ai J, Geng M, Duan W. ACS Med. Chem. Lett. 2016; 7: 629

2 El-Borai MA, Awad MK, Rizk HF, Atlam FM. Curr. Org. Synth. 2018; 15: 275
3 Hu Y, Kitamura N, Musharrafieh R, Wang J. J. Med. Chem. 2021; 64: 8755
4 Miyachi H, Yuzuriha T, Tabata R, Fukuda S, Nunomura K, Lin B, Kobayashi T, Ishimoto K, Doi T, Tachibana K. Bioorg. Med. Chem. Lett. 2019; 29: 2124
5 Goda FE, Abdel-Aziz AA.-M, Attef OA. Bioorg. Med. Chem. 2004; 12: 1845
6 Chandak N, Kumar S, Kumar P, Sharma C, Aneja KR, Sharma PK. Med. Chem. Res. 2013; 22: 5490

7a Saito MS, Lourenço AL, Dias LR. S, Freitas AC. C, Vitorino MI, Albuquerque MG, Rodrigues CR, Cabral LM, Dias EP, Castro HC, Satlher PC. J. Enzyme Inhib. Med. Chem. 2016; 31: 1591
7b da Silva Lima CH, de Araujo Vanelis Soares JC, de Ribeiro JL, Muri EM. F, de Albuquerque S, Dias LR. S. Lett. Drug Des. Discovery 2020; 17: 184

8a Zhong Y.-L, Lindale MG, Yasuda N. Tetrahedron Lett. 2009; 50: 2293
8b Faarasse S, El-Kazzouli S, Naas M, Jouha J, Suzenet F, Guillaumet G. J. Org. Chem. 2017; 82: 12300
8c Lavecchia G, Berteina-Raboin S, Guillaumet G. Tetrahedron Lett. 2004; 45: 2389

9a El-Emary TI. J. Chin. Chem. Soc. (Weinheim, Ger.) 2007; 54: 507
9b Ghaedi A, Bardajee GR, Mirshokrayi A, Mahdavi M, Shafiee A, Akbarzadeh T. RSC Adv. 2015; 5: 89652

10a Maqbool T, Khan MA, Khan MN, Elliott MC, Munawar MA, Nasrullah M, Bhatti AW, Nazeer A, Lin WO. Asian J. Chem. 2013; 25: 7715
10b Prakash R, Shekarrao K, Saikia P, Gogoi S, Boruah RC. RSC Adv. 2015; 5: 21099
10c Zhou Y, Wang L.-S, Lei S.-G, Gao Y.-X, Ma J.-T, Yu Z.-C, Wu Y.-D, Wu A.-X. Org. Chem. Front. 2022; 9: 4416

For representative examples, see:

11a Yao B, Miao T, Wei W, Li P, Wang L. Org. Lett. 2019; 21: 9291
11b Huang C.-Y, Kang H, Li J, Li C.-J. J. Org. Chem. 2019; 84: 12705
11c Pannilawithana N, Yi CS. ACS Catal. 2020; 10: 5852
11d Jha P, Husen S, Kumar R. Green Chem. 2021; 23: 2950
11e Fu L, Liu Y, Wan J.-P. Org. Lett. 2021; 23: 4363
11f Wu Y.-X, Huang M.-H, Peng K, Shi Z, Hao E.-J, Dong Z.-B. J. Org. Chem. 2022; 87: 2446
11g Takeda A, Okai H, Watabe K, Iida H. J. Org. Chem. 2022; 87: 10372
11h Lasso JD, Castillo-Pazos DJ, Li C.-J. Chem. Soc. Rev. 2021; 50: 10955
11i Batra A, Singh KN. Eur. J. Org. Chem. 2020; 43: 6676
11j Maikhuri VK, Maity J, Srivastava S, Prasad AK. Org. Biomol. Chem. 2022; 20: 9522

12 Tao Y, Gu H, Xia H, Yang H, Li J, Xu X, Cheng D. Eur. J. Org. Chem. 2023; e202201480

13a Khatun N, Banerjee A, Santra SK, Ali W, Patel BK. RSC Adv. 2015; 5: 36461
13b Mahesh D, Sadhu P, Punniyamurthy T. J. Org. Chem. 2016; 81: 3227
13c Khemnar AB, Bhanage BM. Org. Biomol. Chem. 2014; 12: 9631
13d Zhu X.-T, Lu Q.-L, Wang X, Zhang T.-S, Hao W.-J, Tu S.-J, Jiang B. J. Org. Chem. 2018; 83: 9890
13e Ratnikov MO, Doyle MP. J. Am. Chem. Soc. 2013; 135: 1549

14 Pyrazolo[3,4-b]pyridines 3a–gg; General Procedure DDQ (0.12 mmol, 1.2 equiv) was added to a solution of the appropriate 1,3-diarylpropene 2 (0.12 mmol, 1.2 equiv) in 1,4-dioxane (3 mL), and the mixture was stirred for 10 min. The appropriate 5-aminopyrazole 1 (0.10 mmol, 1.0 equiv) was then added, and the mixture was stirred at r.t. for 2 h. Cu(OTf)₂ (0.02 mmol, 0.2 equiv) and a solution of TBHP (0.2 mmol, 2.0 equiv) in decane (0.02 mL) were added, and the resultant mixture was stirred at 80 °C (oil bath) for 1 h. When the reaction was complete, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography [silica gel (200–300 mesh), PE–EtOAc (10:1–60:1)]. 1,3,4,6-Tetraphenyl-1H-pyrazolo[3,4-b]pyridine (3a) ¹⁵ Light-yellow solid; yield: 33.8 mg (80%). ¹H NMR (400 MHz, CDCl₃): δ = 8.63–8.60 (m, 2 H), 8.33–8.30 (m, 2 H), 7.79 (s, 1 H), 7.68–7.53 (m, 5 H), 7.44–7.25 (m, 9 H), 7.22–7.18 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 156.71, 152.02, 146.64, 145.90, 139.79, 139.11, 137.48, 133.00, 129.60, 129.36, 129.26, 129.02, 128.89, 128.42, 128.03, 127.82, 127.68, 127.63, 125.85, 121.56, 116.07, 112.20. HRMS (ESI): m/z [M + H]⁺ calcd for C₃₀H₂₂N₃: 424.1808; found: 424.1808.
15 Saleh TS, Eldebss TM. A, Albishri HM. Ultrason. Sonochem. 2012; 19: 49

Supplementary Material

Supporting Information