Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2021; 32(12): 1201-1206
DOI: 10.1055/a-1506-4509
DOI: 10.1055/a-1506-4509
letter
Diastereoselective Synthesis of Spiropyrazolones via 1,3-Dipolar [3+2] Cycloadditions between Pyrazolone-Based Olefins and N,N′-Cyclic Azomethine Imines
We thank the Beijing Municipal Commission of Education (JC015001200902), the Beijing Municipal Natural Science Foundation (7102010, 2122008, and 2172003), the Basic Research Foundation of Beijing University of Technology (X4015001201101), the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality (PHR201008025), the Doctoral Scientific Research Start-up Foundation of Beijing University of Technology (52015001200701) for financial supports.
Abstract
Under the catalysis of PhCO2H, the 1,3-dipolar [3+2] cycloaddition between pyrazolone-based olefins and N,N′-cyclic azomethine imines proceeded readily, thus delivering structurally novel spiropyrazolones with up to 98% yield and >20:1 dr. The relative stereochemical configuration of the obtained spiropyrazolones was unambiguously assigned by X-ray single-crystal structure analysis. The diastereoselective formation of the title spiropyrazolones was interpreted by the hypothesized reaction mechanism.
Key words
1,3-dipolar [3+2] cycloaddition - pyrazolone-based olefin - N,N′-cyclic azomethine imine - spiropyrazolone - diastereoselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1506-4509.
- Supporting Information
Publication History
Received: 16 April 2021
Accepted after revision: 11 May 2021
Accepted Manuscript online:
11 May 2021
Article published online:
15 June 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References and Notes
- 1a Wu S, Li Y, Xu G, Chen S, Zhang Y, Liu N, Dong G, Miao C, Su H, Zhang W, Sheng C. Eur. J. Med. Chem. 2016; 115: 141
- 1b Zhang Y, Wu S, Wang S, Fang K, Dong G, Liu N, Miao Z, Yao J, Li J, Zhang W, Sheng C, Wang W. Eur. J. Org. Chem. 2015; 2030
- 1c 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
- 1d Chande MS, Barve PA, Suryanarayan V. J. Heterocycl. Chem. 2007; 44: 49
-
1e
Han B,
Xu S,
Wang P.
CN 104610148, 2015
-
1f
Silaychev PS,
Filimonov VO,
Maslivets AN,
Makhmudov RR.
RU 2577528, 2014
- 1g Bao X, Wei S, Qian X, Qu J, Wang B, Zou L, Ge G. Org. Lett. 2018; 20: 3394
- 2a Xie X, Xiang L, Peng C, Han B. Chem. Rec. 2019; 19: 2209
- 2b Awasthi A, Yadav P, Kumar V, Tiwari DK. Adv. Synth. Catal. 2020; 362: 4378
- 2c Zhang J, Chan W.-L, Chen L, Ullah N, Lu Y. Org. Chem. Front. 2019; 6: 2210
- 2d Cheng C, Sun X, Miao Z. Org. Biomol. Chem. 2020; 18: 5577
- 2e Lin Y, Zhao B.-L, Du D.-M. J. Org. Chem. 2019; 84: 10209
- 2f Chen N, Zhu L, Gan L, Liu Z, Wang R, Cai X, Jiang X. Eur. J. Org. Chem. 2018; 2939
- 2g Maity R, Sahoo SC, Pan SC. Eur. J. Org. Chem. 2019; 2297
- 2h Wang C, Wen D, Chen H, Deng Y, Liu X, Liu X, Wang L, Gao F, Guo Y, Sun M, Wang K, Yan W. Org. Biomol. Chem. 2019; 17: 5514
- 3a Mao B, Liu H, Yan Z, Xu Y, Xu J, Wang W, Wu Y, Guo H. Angew. Chem. Int. Ed. 2020; 59: 11316
- 3b da Silva AF, Leonarczyk IA, Ferreira MA. B, Jurberg ID. Org. Chem. Front. 2020; 7: 3599
- 3c Meninno S, Mazzanti A, Lattanzi A. Adv. Synth. Catal. 2019; 361: 79
- 3d Zhang Y, Wang C, Huang W, Haruehanroengra P, Peng C, Sheng J, Han B, He G. Org. Chem. Front. 2018; 5: 2229
- 3e Zhao C, Shi K, He G, Gu Q, Ru Z, Yang L, Zhong G. Org. Lett. 2019; 21: 7943
- 3f Mondal B, Maity R, Pan SC. J. Org. Chem. 2018; 83: 8645
- 3g Liang J.-Y, Shen S.-J, Chai X.-Q, Lv T. J. Org. Chem. 2018; 83: 12744
- 3h Luo W, Shao B, Li J, Xiao X, Song D, Ling F, Zhong W. Org. Chem. Front. 2020; 7: 1016
- 4a Li H, Gontla R, Flegel J, Merten C, Ziegler S, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2019; 58: 307
- 4b Leng H.-J, Li Q.-Z, Zeng R, Dai Q.-S, Zhu H.-P, Liu Y, Huang W, Han B, Li J.-L. Adv. Synth. Catal. 2018; 360: 229
- 4c Xu J, Hu L, Hu H, Ge S, Liu X, Feng X. Org. Lett. 2019; 21: 1632
- 4d Sun B.-B, Chen J.-B, Zhang J.-Q, Yang X.-P, Lv H.-P, Wang Z, Wang X.-W. Org. Chem. Front. 2020; 7: 796
- 4e Sun B.-B, Zhang J.-Q, Chen J.-B, Fan W.-T, Yu J.-Q, Hu J.-M, Wang X.-W. Org. Chem. Front. 2019; 6: 1842
- 4f Ji Y.-L, Li H.-P, Ai Y.-Y, Li G, He X.-H, Huang W, Huang R.-Z, Han B. Org. Biomol. Chem. 2019; 17: 9217
- 4g Krishna AV, Reddy GS, Gorachand B, Ramachary DB. Eur. J. Org. Chem. 2020; 6623
- 5a Li X, Chen F.-Y, Kang J.-W, Zhou J, Peng C, Huang W, Zhou M.-K, He G, Han B. J. Org. Chem. 2019; 84: 9138
- 5b Khairnar PV, Wu C.-Y, Lin Y.-F, Edukondalu A, Chen Y.-R, Lin W. Org. Lett. 2020; 22: 4760
- 6a Cheng C, Zhang J, Wang X, Miao Z. J. Org. Chem. 2018; 83: 5450
- 6b Du J, Wu J.-H, Zhu L, Ren X, Jiang C, Wang T. Adv. Synth. Catal. 2020; 362: 2510
- 6c Cheng C, Sun X, Wu Z, Liu Q, Xiong L, Miao Z. Org. Biomol. Chem. 2019; 17: 3232
- 6d Shi Q, Zhang W, Wang Y, Qu L, Wei D. Org. Biomol. Chem. 2018; 16: 2301
- 6e Xu J, Yang W, Shi W, Mao B, Lin Y, Xiao Y, Guo H. Tetrahedron 2019; 75: 3609
- 6f Mutyala R, Reddy VR, Donthi R, Kallaganti VS. R, Chandra R. Tetrahedron Lett. 2019; 60: 703
- 6g Wang D, Wang X, Zhang XG, Miao ZW. Synthesis 2019; 51: 2149
- 6h Tan F, Su S, Liu Z. J. Heterocycl. Chem. 2020; 57: 2904
- 7a Požgan F, Al Mamari H, Grošelj U, Svete J, Štefane B. Molecules 2018; 23: 3
- 7b Xu X, Qian Y, Zavalij PY, Doyle MP. J. Am. Chem. Soc. 2013; 135: 1244
- 7c Gong J, Wan Q, Kang Q. Org. Lett. 2018; 20: 3354
- 7d Tong TM. T, Soeta T, Suga T, Kawamoto K, Hayashi Y, Ukaji Y. J. Org. Chem. 2017; 82: 1969
- 7e Volpe C, Meninno S, Capobianco A, Vigliotta G, Lattanzi A. Adv. Synth. Catal. 2019; 361: 1018
- 7f Fang Q.-Y, Jin H.-S, Wang R.-B, Zhao L.-M. Chem. Commun. 2019; 55: 10587
- 7g Li C, Wang C.-S, Li T.-Z, Mei G.-J, Shi F. Org. Lett. 2019; 21: 598
- 7h Yang Q.-Q, Yin X, He X.-L, Du W, Chen Y.-C. ACS Catal. 2019; 9: 1258
-
8
Typical Procedure and Characterization Data for 3aa
A mixture of pyrazolone-based olefin 1a (1.0 equiv, 0.1 mmol), N,N′-cyclic azomethine imine 2a (1.25 equiv, 0.125 mmol), and PhCO2H (20.0 mol%) in toluene (1.0 mL) was stirred at 110 ℃. After the reaction was completed as indicated by TLC plate, the solvent was removed by evaporation and the resulted crude product was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate, 4:1 to 2:1) to afford product trans-3aa (92% yield).
Compound 3aa: white solid, yield 40.1 mg, 92%; mp 157.2–157.4 ℃. 1H NMR (400 MHz, CDCl3): δ = 7.82 (d, J = 7.6 Hz, 2 H), 7.44 (t, J = 8.0 Hz, 2 H), 7.33–7.24 (m, 9 H), 7.17 (d, J = 7.2 Hz, 2 H), 5.78 (s, 1 H), 4.43 (s, 1 H), 3.97–3.91 (m, 1 H), 3.28–3.21 (m, 1 H), 3.11–3.03 (m, 1 H), 3.00–2.91 (m, 1 H), 1.53 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 173.6, 170.9, 159.5, 137.4, 135.4, 131.9, 129.1, 129.0, 128.94, 128.90, 128.2, 126.1, 125.7, 125.1, 119.3, 77.5, 72.9, 63.9, 47.9, 32.0, 17.2 ppm. HRMS (ESI): m/z calcd for C27H25N4O2 [M + H]+: 437.1972; found: 437.1964.
-
9 CCDC 2065581 (trans-3ak) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/structures.
For selected examples, see:
For a review, see:
For selected examples, see:
For selected examples, see:
For selected examples, see:
For examples, see:
For selected examples, see:
For a review, see:
For selected examples, see: