3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Methods
3.2. General Procedure for the Cycloaddition of Alkenes and α-Nitroketones
3.2.1. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (3a)
3.2.2. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(2-bromophenyl)methanone (3b)
3.2.3. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(3-bromophenyl)methanone (3c)
3.2.4. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(4-bromophenyl)methanone (3d)
3.2.5. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(p-tolyl)methanone (3e)
3.2.6. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(4-methoxyphenyl)methanone (3f)
3.2.7. (5-Benzyl-4,5-dihydroisoxazol-3-yl)(4-tert-butylphenyl)methanone (3g)
3.2.8. [1,1′-Biphenyl]-4-yl(5-benzyl-4,5-dihydroisoxazol-3-yl)methanone (3h)
3.2.9. Methyl 5-benzyl-4,5-dihydroisoxazole-3-carboxylate (3i)
3.2.10. (5-(2-Methylbenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5a)
3.2.11. (5-(3-Methylbenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5b)
3.2.12. (5-(4-Methylbenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5c)
3.2.13. (5-(4-Methoxybenzyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5d)
3.2.14. (5-Octyl-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5e)
3.2.15. (5-(Chloromethyl)-4,5-dihydroisoxazol-3-yl)(phenyl)methanone (5f)
3.2.16. (3a,4,5,6,7,7a-Hexahydrobenzo[d]isoxazol-3-yl)(phenyl)methanone (5g)
3.2.17. Ethyl 3-benzoyl-4,5-dihydroisoxazole-5-carboxylate (7a)
3.2.18. (5-Butylisoxazol-3-yl)(phenyl)methanone (7b)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Chen, C.-H.; Wu, Q.-Y.; Wei, C.; Liang, C.; Su, G.-F.; Mo, D.-L. Iron(iii)-catalysed selective N–O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from N-vinyl-α,β-unsaturated ketonitrones. Green Chem. 2018, 20, 2722–2729. [Google Scholar] [CrossRef]
- Zhang, L.H.; Chung, J.C.; Costello, T.D.; Valvis, I.; Ma, P.; Kauffman, S.; Ward, R. The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist. J. Org. Chem. 1997, 62, 2466–2470. [Google Scholar] [CrossRef]
- Sun, R.; Li, Y.; Xiong, L.; Liu, Y.; Wang, Q. Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Isoxazoline and Isoxazole Group. J. Agric. Food Chem. 2011, 59, 4851–4859. [Google Scholar] [CrossRef]
- Ismail, T.; Shafi, S.; Singh, S.; Sidiq, T.; Khajuria, A.; Rouf, A.; Yadav, M.; Saikam, V.; Singh, P.P.; Alam, M.S.; et al. Synthesis and immunopotentiating activity of novel isoxazoline functionalized coumarins. Eur. Med. Chem. 2016, 123, 90–104. [Google Scholar] [CrossRef]
- Kamal, A.; Reddy, J.S.; Ramaiah, M.J.; Dastagiri, D.; Bharathi, E.V.; Azhar, M.A.; Sultana, F.; Pushpavalli, S.N.C.V.L.; Pal-Bhadra, M.; Juvekar, A.; et al. Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents. Eur. J. Med. Chem. 2010, 45, 3924–3937. [Google Scholar] [CrossRef]
- Kim, B.H.; Chung, Y.J.; Ryu, E.J. Synthesis of α-hydroxy ketomethylene dipeptide isosteres. Tetrahedron Lett. 1993, 34, 8465–8468. [Google Scholar]
- Curran, D.P. Reduction of. DELTA. 2-isoxazolines. 3. Raney nickel catalyzed formation of. beta.-hydroxy ketones. J. Am. Chem. Soc. 1983, 105, 5826–5833. [Google Scholar] [CrossRef]
- Curran, D.P.; Kim, B.H. Reduction of 4,5-Dihydro-1,2-oxazoles (Δ-Isoxazolines); A Cycloadditive Approach to 2-Alkenyl Ketones. Synthesis 1986, 4, 312–315. [Google Scholar] [CrossRef]
- Kozikowski, A.P.; Stein, P.D. The INOC route to carbocyclics: A formal total synthesis of (±)-sarkomycin. J. Am. Chem. Soc. 1982, 104, 4023–4024. [Google Scholar] [CrossRef]
- Muri, D.; Carreira, E.M. Stereoselective Synthesis of Erythronolide A via Nitrile Oxide Cycloadditions and Related Studies. J. Org. Chem. 2009, 74, 8695–8712. [Google Scholar] [CrossRef]
- Choe, H.; Cho, H.; Ko, H.-J.; Lee, J. Total Synthesis of (+)-Pochonin D and (+)-Monocillin II via Chemo-and Regioselective Intramolecular Nitrile Oxide Cycloaddition. Org. Lett. 2017, 19, 6004–6007. [Google Scholar] [CrossRef]
- Choe, H.; Pham, T.T.; Lee, J.Y.; Latif, M.; Park, H.; Kang, Y.K.; Lee, J. Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (−)-11β-Hydroxycurvularin. J. Org. Chem. 2016, 81, 2612–2617. [Google Scholar] [CrossRef]
- Gothelf, K.V.; Jørgensen, K.A. Asymmetric 1,3-Dipolar Cycloaddition Reactions. Chem. Rev. 1998, 98, 863–910. [Google Scholar] [CrossRef]
- Collington, E.W.; Knight, J.G.; Wallis, C.J.; Warren, S. Regiospecific synthesis of (E) unsaturated 3,5-dialkyl-isoxazoles and derived leukotriene analogues using phosphine oxides. Tetrahedron Lett. 1989, 30, 877–880. [Google Scholar] [CrossRef]
- Nazarenko, K.G.; Shvidenko, K.V.; Pinchuk, A.M.; Tolmachev, A.A. Synthesis of 7-Amino-1-nitro-2-heptanone Derivatives. Synth. Commun. 2003, 33, 4241–4252. [Google Scholar] [CrossRef]
- Shimizu, T.; Hayashi, Y.; Teramura, K. The Reaction of Primary Nitro Compounds with Dipolarophiles in the Presence of p-Toluenesulfonic Acid. Bull. Chem. Soc. Jpn. 1984, 57, 2531–2534. [Google Scholar] [CrossRef] [Green Version]
- Wade, P.A.; Amin, N.V.; Yen, H.K.; Price, D.T.; Huhn, G.F. Acid-catalyzed nitronate cycloaddition reactions. Useful syntheses and simple transformations of 3-acyl- and 3-alkenylisoxazolines. J. Org. Chem. 1984, 49, 4595–4601. [Google Scholar] [CrossRef]
- Itoh, K.-i.; Aoyama, T.; Satoh, H.; Fujii, Y.; Sakamaki, H.; Takido, T.; Kodomari, M. Application of silica gel-supported polyphosphoric acid (PPA/SiO2) as a reusable solid acid catalyst to the synthesis of 3-benzoylisoxazoles and isoxazolines. Tetrahedron Lett. 2011, 52, 6892–6895. [Google Scholar] [CrossRef]
- Yavari, I.; Piltan, M.; Moradi, L. Synthesis of pyrrolo[2,1-a]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline. Tetrahedron 2009, 65, 2067–2071. [Google Scholar] [CrossRef]
- Machetti, F.; Cecchi, L.; Trogu, E.; De Sarlo, F. Isoxazoles and Isoxazolines by 1,3-Dipolar Cycloaddition: Base-Catalysed Condensation of Primary Nitro Compounds with Dipolarophiles. Eur. J. Org. Chem. 2007, 2007, 4352–4359. [Google Scholar] [CrossRef]
- Cecchi, L.; De Sarlo, F.; Machetti, F. Synthesis of 4,5-Dihydroisoxazoles by Condensation of Primary Nitro Compounds with Alkenes by Using a Copper/Base Catalytic System. Chem. A Eur. J. 2008, 14, 7903–7912. [Google Scholar] [CrossRef]
- Umemoto, N.; Imayoshi, A.; Tsubaki, K. Nitrile oxide cycloaddition reactions of alkenes or alkynes and nitroalkanes substituted with O-alkyloxime groups convertible to various functional groups. Tetrahedron Lett. 2020, 61, 152213–152216. [Google Scholar] [CrossRef]
- Lee, J.J.; Kim, J.; Jun, Y.M.; Lee, B.M.; Kim, B.H. Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones. Tetrahedron 2009, 65, 8821–8831. [Google Scholar] [CrossRef]
Entry | Catalyst | Amount of Base (mol) | Yield b (%) of 3a |
---|---|---|---|
1 | -- | -- | <5 |
2 | Imidazole | 0.5 | 43 |
3 | 4-Dimethylaminopyridine | 0.5 | 45 |
4 | Triethylamine | 0.5 | 55 |
5 | N,N,N’,N’-Tetramethylethylenediamine | 0.5 | 48 |
6 | Chloramine-T | 0.5 | 77 |
7 | Chloramine-T | 1.0 | 52 |
8 | Chloramine-T | 0.25 | 68 |
9 | Chloramine-T | 0.1 | 65 |
10 c | Chloramine-T | 0.5 | 46 |
11 d | Chloramine-T | 0.5 | 40 |
12 e | Chloramine-T | 0.5 | 11 |
13 f | Chloramine-T | 0.5 | 36 |
14 g | Chloramine-T | 0.5 | 70 |
15 h | Chloramine-T | 0.5 | 59 |
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Pan, X.; Xin, X.; Mao, Y.; Li, X.; Zhao, Y.; Liu, Y.; Zhang, K.; Yang, X.; Wang, J. 3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles. Molecules 2021, 26, 3491. https://doi.org/10.3390/molecules26123491
Pan X, Xin X, Mao Y, Li X, Zhao Y, Liu Y, Zhang K, Yang X, Wang J. 3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles. Molecules. 2021; 26(12):3491. https://doi.org/10.3390/molecules26123491
Chicago/Turabian StylePan, Xinhui, Xiaobing Xin, Ying Mao, Xin Li, Yanan Zhao, Yidi Liu, Ke Zhang, Xiaoda Yang, and Jinhui Wang. 2021. "3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles" Molecules 26, no. 12: 3491. https://doi.org/10.3390/molecules26123491