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Synthesis 2019; 51(06): 1473-1481
DOI: 10.1055/s-0037-1610999
DOI: 10.1055/s-0037-1610999
paper
Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core
The authors thank CSIR, New Delhi for financial support as part of the XII five-year plan program under the title ACT ().Further Information
Publication History
Received: 01 August 2018
Accepted after revision: 05 September 2018
Publication Date:
14 November 2018 (online)
Abstract
A novel, one-pot reaction for the synthesis of 3,4-dihydroisoquinolin-2(1H)-one derivatives is developed via a base-mediated three-component reaction of ninhydrin, aniline and acetylenic esters. This diastereoselective reaction takes place in methanol at 70 °C under transition-metal-free conditions, and direct construction of the C–N and C–C bonds is readily achieved via tandem cyclization. These cyclic frameworks are resourceful small molecular keys to many natural products.
Key words
ninhydrin - anilines - 3,4-dihydroisoquinolin-2(1H)-ones - methanolysis - tandem cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610999.
- Supporting Information
- CIF File
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References
- 1a Pettit GR. Ducki S. Eastham SA. Melody N. J. Nat. Prod. 2009; 72: 1279
- 1b Jin Z. Nat. Prod. Rep. 2013; 30: 849
- 2a Cappelli A. Pericot Mohr G. Giuliani G. Galeazzi S. Anzini M. Mennuni L. Ferrari F. Makovec F. Kleinrath EM. Langer T. Valoti M. Giorgi G. Vomero S. J. Med. Chem. 2006; 49: 6451
- 2b Khadka DB. Yang SH. Cho SH. Zhao C. Cho W.-J. Tetrahedron 2012; 68: 250
- 2c Matsui T. Sugiura T. Nakai H. Iguchi S. Shigeoka S. Takada H. Odagaki Y. Nagao Y. Ushio Y. J. Med. Chem. 1992; 35: 3307
- 3a Thompson RC. Kallmerten J. J. Org. Chem. 1990; 55: 6076
- 3b Asano Y. Kitamura S. Ohra T. Itoh F. Kajino M. Tamura T. Kaneko M. Ikeda S. Igata H. Kawamoto T. Sogabe S. Matsumoto S. Tanaka T. Yamaguchi M. Kimura H. Fukumoto S. Bioorg. Med. Chem. 2008; 16: 4699
- 3c Snow RJ. Cardozo MG. Morwick TM. Busacca CA. Dong Y. Echner RJ. Jakes S. Kapadia S. Lukas S. Moss N. Panzenbeck M. Peet GW. Peterson JD. Prokopowicz AP. Sellati R. Tschantz MA. J. Med. Chem. 2002; 45: 3394
- 4a Krane BD. Shamma M. J. Nat. Prod. 1982; 45
- 4b Chern MS. Li WR. Tetrahedron Lett. 2004; 45: 8323
- 4c Xiang Z. Luo T. Lu K. Cui J. Shi X. Fathi R. Chen J. Yang Z. Org. Lett. 2004; 6: 3155
- 5 Umarov KS. Ismailov ZF. Yunusov SY. Chem. Nat. Compd. 1973; 6: 452
- 6 Leese MP. Jourdan FL. Major MR. Dohle W. Thomas MP. Hamel E. Ferrandis E. Mahon MF. Newman SP. Purohit A. Potter BV. L. ChemMedChem 2014; 9: 798
- 7 Zhou D. Gross JL. Adedoyin AB. Aschmies SB. Brennan J. Bowlby M. Di L. Kubek K. Platt BJ. Wang Z. Zhang G. Brandon N. Comery TA. Robichaud AJ. J. Med. Chem. 2012; 55: 2452
- 8a Billamboz M. Bailly F. Lion C. Touati N. Vezin H. Calmels C. Andreola M. Christ F. Debyser Z. Cotelle P. J. Med. Chem. 2011; 54: 1812
- 8b Billamboz M. Suchaud V. Bailly F. Lion C. Demeulemeester J. Calmels C. Andreola M. Christ F. Debyser Z. Cotelle P. ACS Med. Chem. 2013; 4: 606
- 8c Tsou H. Otteng M. Tran T. Floyd MB. Reich MJr. Birnberg G. Kutterer K. Kaloustian SA. Ravi M. Nilakantan R. Grillo M. McGinnis JP. Rabindran SK. J. Med. Chem. 2008; 51: 3507
- 8d Komoda M. Kakuta H. Takahashi H. Fujimoto Y. Kadoya S. Kato F. Hashimoto Y. Bioorg. Med. Chem. 2001; 9: 121
- 9a Guimond N. Gorelsky SI. Fagnou K. J. Am. Chem. Soc. 2011; 133: 6449
- 9b Xia D. Li Y. Miao T. Lia P. Wang L. Chem. Commun. 2016; 52: 11559
- 9c Zhou W. Ni S. Mei H. Han J. Pan Y. Org. Lett. 2015; 17: 2724
- 9d Yoon H. Petrone DA. Lautens M. Org. Lett. 2014; 16: 6420
- 9e Bai P. Huang KL. Synthesis 2017; 49: 5357
- 9f Tazawa A. Ando J. Ishizawa K. Azumaya I. Hikawa H. Tanaka M. RSC Adv. 2018; 8: 6146
- 10 Shirsat PK. Khomane NB. Mali PR. Reddy Maddi R. Nanubolu JB. Meshram HM. ChemistrySelect 2017; 2: 11218
- 11a Peng S. Liu S. Zhang S. Cao S. Sun J. Org. Lett. 2015; 17: 5032
- 11b Qiu Y.-F. Zhu X.-Y. Li Y.-X. He Y.-T. Yang F. Wang J. Hua H.-L. Zheng L. Wang L.-C. Liu X.-Y. Liang Y.-M. Org. Lett. 2015; 17: 3694
- 11c Sang P. Xie Y. Zou J. Zhang Y. Adv. Synth. Catal. 2012; 354: 1873
- 11d Yi X. Xi C. Org. Lett. 2015; 17: 5836
- 11e Li J. Huang R. Xing Y.-K. Qiu G. Tao H.-Y. Wang C.-J. J. Am. Chem. Soc. 2015; 137: 10124
- 12a Würtz S. Rakshit S. Neumann JJ. Droge T. Glorius F. Angew. Chem. Int. Ed. 2008; 47: 7230
- 12b Varala R. Nuvula S. Adapa SR. Aust. J. Chem. 2006; 59: 921
- 12c Jenner G. Tetrahedron Lett. 1996; 37: 3691
- 13a Sagar A. Vidaycharan S. Shinde AH. Sharada DS. Org. Biomol. Chem. 2016; 14: 4018
- 13b Choudhary G. Peddinti RK. Green Chem. 2011; 13: 3290
- 13c Brandt CA. da Silva AC. M. P. Pancote CG. Brito CL. da Silveira MA. B. Synthesis 2004; 1557
- 14 Yavari I. Seyfi S. Nematpour M. Hossaini Z. Helv. Chim. Acta 2010; 93: 1413
- 15a Sun M.-Y. Meng X.-Y. Zhao F.-J. Dang Y.-J. Jiang F. Liu K. Wang C.-S. Jiang B. Tu S.-J. Eur. J. Org. Chem. 2014; 3690
- 15b Muthusaravanan S. Sasikumar C. Bala BD. Perumal S. Green Chem. 2014; 16: 1297
- 15c Yavari I. Arab-Salmanabadi S. Aminkhani A. J. Iran Chem. Soc. 2012; 9: 503
- 15d Alizadeh A. Ghanbaripour R. Feizabadi M. Zhu L.-G. Dusek M. RSC Adv. 2015; 5: 80518