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-00000084.xml
Synthesis 2019; 51(07): 1669-1679
DOI: 10.1055/s-0037-1610676
DOI: 10.1055/s-0037-1610676
paper
Lewis Acid Catalyzed Regio- and Diastereoselective Synthesis of Spiroisoxazolines via One-Pot Sequential Knoevenagel Condensation/1,3-Dipolar Cycloaddition Reaction
We gratefully acknowledge the financial support from the Research Council of Shahid Beheshti University and the Iran National Science Foundation (INSF) (Project Number 96011205).Further Information
Publication History
Received: 31 October 2018
Accepted after revision: 08 November 2018
Publication Date:
09 January 2019 (online)
Abstract
A ZnCl2-catalyzed regio- and diastereoselective one-pot sequential Knoevenagel condensation/1,3-dipolar cycloaddition reaction of CH acids (oxindole, 1,3-indandione, and 3H-pyrazol-3-one), aldehydes, and dibromoformaldoxime has been established. The method allows the synthesis of diversely functionalized spiroisoxazolines in good isolated yields under mild reaction conditions. Moreover, the preparation of spiroindene-isoxazole-1,3-diones containing benzoimidazole or benzothiazole moieties as new ligands for the metal-catalyzed coupling reactions and C–H activation is demonstrated.
Keywords
1,3-dipolar cycloaddition reaction - isoxazolines - nitrile oxides - spirooxindoles - spiroindandiones - coupling reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610676.
- Supporting Information
-
References
- 1a Borah A, Sharma A, Hazarika H, Sharma K, Gogoi P. J. Org. Chem. 2017; 82: 8309
- 1b Vohra RK, Bruneau C, Renaud J.-L. Adv. Synth. Catal. 2006; 348: 2571
- 1c Zulfiqara F, Kitazume T. Green Chem. 2000; 2: 296
- 1d Mostafa MA. B, Calder ED. D, Racys DT, Sutherland A. Chem. Eur. J. 2017; 23: 1044
- 2a Barluenga J, Vázquez-Villa H, Ballesteros A, González JM. Adv. Synth. Catal. 2005; 347: 526
- 2b Ramachary DB, Jain S. Org. Biomol. Chem. 2011; 9: 1277
- 3a Bunce RA. Tetrahedron 1995; 51: 13103
- 3b McCarroll AJ, Walton JC. Angew. Chem. Int. Ed. 2001; 40: 2224
- 3c Gilbert BC, Parsons AF. J. Chem. Soc., Perkin Trans. 2 2002; 367
- 4a Balalaie S, Shamakli M, Nikbakht A, Alavijeh NS, Rominger F, Rostamizadeha S, Bijanzadeh HR. Org. Biomol. Chem. 2017; 15: 5737
- 4b Harigae R, Moriyama K, Togo H. J. Org. Chem. 2014; 79: 2049
- 4c Chen W, Zhang J, Wang B, Zhao Z, Wang X, Hu Y. J. Org. Chem. 2015; 80: 2413
- 4d Akritopoulou-Zanze I, Gracias V, Moore JD, Djuric SW. Tetrahedron Lett. 2004; 45: 3421
- 4e Alaoui S, Driowya M, Demange L, Benhida R, Bougrin K. Ultrason. Sonochem. 2018; 40: 289
- 4f Maheswari SU, Perumal S. Tetrahedron Lett. 2012; 53: 6885
- 4g Harigae R, Moriyama K, Togo H. J. Org. Chem. 2014; 79: 2049
- 5a Smietana M, Gouverneur V, Mioskowski C. Tetrahedron Lett. 1999; 40: 1291
- 5b Bennani B, Kerbal A, Ben Larbi N, Ben Hadda T. Moroccan Patent No. 2769, 2004
- 5c Howe RK, Shelton BR. J. Org. Chem. 1990; 55: 4603
- 5d Cue D, Southern SO, Southern PJ, Prabhakar J, Lorelli W, Smallheer JM, Mousa SA, Cleary PP. Proc. Natl. Acad. Sci.U. S. A. 2000; 97: 2858
- 5e Compagnone RS, Avila R, Suárez AI, Abrams OV, Rangel HR, Arvelo F, Piña IC, Merentes EE. J. Nat. Prod. 1999; 62: 1443
- 5f Moody K, Thomson RH, Fattorusso E, Minale L, Sodano G. J. Chem. Soc., Perkin Trans. 1 1972; 18
- 5g Tsukamoto S, Kato H, Hirota H, Fusetani N. Tetrahedron 1996; 52: 8181
- 5h Liu Y, Li H, Zhou X, He Z. J. Org. Chem. 2017; 82: 10997
- 6 Das P, Omollo AO, Sitole LJ, McClendon E, Valente EJ, Raucher D, Walker LR, Hamme AT. II. Tetrahedron Lett. 2015; 56: 1794
- 7 Arai MA, Arai T, Sasai H. Org. Lett. 1999; 1: 1795
- 8a Ramírez-Monroy A, Swager TM. Organometallics 2011; 30: 2464
- 8b Zhang X.-P, Liu J, Zhang J.-X, Huang J.-H, Wan C.-Z, Li C.-H, You X.-Z. Polyhedron 2013; 60: 85
- 8c Koranne PS, Tsujihara T, Arai MA, Bajracharya GB, Suzuki T, Onitsuka K, Sasai H. Tetrahedron: Asymmetry 2007; 18: 919
- 8d Takenaka K, Mohanta SC, Patil ML, Rao CL, Takizawa S, Suzuki T, Sasai H. Org. Lett. 2010; 12: 3480
- 8e Jracharya GB, Koranne PS, Tsujihara T, Takizawa S, Onitsuka K, Sasai H. Synlett 2009; 310
- 8f Guo J.-Y, Minko Y, Santiago CB, Sigman MS. ACS Catal. 2017; 7: 4144
- 8g Zhu R, Buchwald SL. J. Am. Chem. Soc. 2015; 137: 8069
- 8h Race NJ, Schwalm CS, Nakamuro T, Sigman MS. J. Am. Chem. Soc. 2016; 138: 15881
- 8i Jiang Z.-Z, Gao A, Li H, Chen D, Ding C.-H, Xu B, Hou X.-L. Chem. Asian J. 2017; 12: 3119
- 9a Said AM, Savage GP. J. Org. Chem. 2011; 76: 6946
- 9b Benltifa M, Vidal S, Gueyrard D, Goekjian PG, Msaddek M, Praly J.-P. Tetrahedron Lett. 2006; 47: 6143
- 9c Lian X, Guo S, Wang G, Lin L, Liu X, Feng X. J. Org. Chem. 2014; 79: 7703
- 9d Soleimani E, Yazdani H, Saei P. Tetrahedron Lett. 2015; 56: 1635
- 10 Adamo MF. A, Donati D, Duffy EF, Sarti-Fantoni P. J. Org. Chem. 2005; 70: 8395
- 11a Ahadi S, Khavasi HR, Bazgir A. Chem. Eur. J. 2013; 19: 12553
- 11b Imani Shakibaei G, Bazgir A. RSC Adv. 2016; 6: 22306
- 12 Shimizu T, Ishizaki M, Nitada N. Chem. Pharm. Bull. 2002; 50: 908 ; and references cited therein
- 13a Wang G, Zhang J, Tang J, Gang Zou G. Adv. Synth. Catal. 2017; 359: 2514
- 13b Shekarrao K, Kaishap PP, Gogoi S, Boruah RC. Adv. Synth. Catal. 2015; 357: 1187
- 13c Li Y, Mao F, Chen T, Zhou Z, Wang Y, Huang J. Adv. Synth. Catal. 2015; 357: 2827
- 14a Yadav MR, Nagaoka M, Kashihara M, Zhong RL, Miyazaki T, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2017; 139: 9423
- 14b Phan NT. N, Sluys MV. D, Jones CW. Adv. Synth. Catal. 2006; 348: 609
- 15 Li Z, Gelbaum C, Heaner WL, Fisk JS, Jaganathan A, Holden B, Pollet P, Liotta CL. Org. Process Res. Dev. 2016; 20: 1489
- 16 Puthiaraj P, Suresha P, Pitchumani K. Green Chem. 2014; 16: 2865
- 17 Li S, Wan P, Ai J, Sheng R, Hu Y, Hu Y. Adv. Synth. Catal. 2017; 359: 772
- 18a Canivet J, Yamaguchi J, Ban I, Itami K. Org. Lett. 2009; 11: 1733
- 18b Yamamoto T, Muto K, Komiyama M, Canivet J, Yamaguchi J, Itami K. Chem. Eur. J. 2011; 17: 10113
- 19 CCDC 1827670 (4g) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 20 CCDC 1827669 (9b) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 21 Hachiya H, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 1737
- 22 Nandurkar NS, Bhanushali MJ, Bhor MD, Bhanage BM. Tetrahedron Lett. 2008; 49: 1045
- 23 Huang J, Chan J, Chen Y, Borths CJ, Baucom KD, Larsen RD, Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
- 24 Naohiro K, Yamamoto Y. Eur. J. Org. Chem. 2009; 1864
- 25 Soleimani E, Khodaei MM, Yazdani H, Saei P, Zavar Reza J. J. Iran. Chem. Soc. 2015; 12: 1281
- 26 Inamoto K, Hasegawa C, Hiroya K, Doi T. Org. Lett. 2008; 10: 5147
- 27 Bandyopadhyay P, Sathe M, Ponmariappan S, Sharma A, Srivastava AK, Kaushik MP. Bioorg. Med. Chem. Lett. 2011; 21: 7306
- 28 Chung HY, Park MH, Ha YM, Han YK, Park JY, Park YJ, Kim JA, Lee JY, Song YM, Moon HR. Patent US 2014/37564, 2014
- 29 Yang Z, Wang A, Chen X, Gui Q, Liu J, Tan Z, Wang H, Shi JC. Synlett 2013; 24: 1549