Scandium(III) triflate mediated intramolecular ring expansion of aziridines: a direct access to 4-aryltetrahydroisoquinolines
Graphical abstract
Section snippets
Acknowledgments
We sincerely appreciate the financial support from Albany Molecular Research Inc. The authors also thank Dr. Chen Zhen Zia for his support and Dr. Isherwood Matthew for useful discussions during the preparation of this manuscript.
References and notes (15)
- et al.
Drugs
(1979) - et al.
Chem. Rev.
(1995) - et al.
Org. Lett.
(2013) - et al.
Chem. Rev.
(2002)et al.Tetrahedron Lett.
(2000)et al.J. Am. Chem. Soc.
(1996)et al.J. Am. Chem. Soc.
(2002)et al.Tetrahedron Lett.
(2001)(f) Liu, S.; Molino, B. F.; Nacro, K. Patent. WO2010132437A1, 2010; Chem. Abstr. 2010, 153,... - et al.
J. Med. Chem.
(1984)et al.Pharm. Sci.
(1997)
Cited by (12)
One-pot reactions of three-membered rings giving N,O,S-heterocycles
2021, Advances in Heterocyclic ChemistryCitation Excerpt :Treatment of the keto epoxides 233 with BF3·Et2O gives ketone intermediates, which intramolecularly cyclize to quinolin-4-ones 234 (Scheme 96) (2016T7025). Recent syntheses of tetrahydroisoquinolines 235–237 are presented in Scheme 97 (2014TL6787, 2016ASC532, 2018AGE10980). Fused piperidines 238 were accessed from vinyl indoles and N-activated aziridines in good yields and with great diastereoselectivity (Scheme 98).
Unlocking the synthetic potential of aziridine and cyclopropane-fused quinolin-2-ones by regioselective fragmentation of its three-membered rings
2020, Arabian Journal of ChemistryCitation Excerpt :Saxagliptin is an oral hypoglycemic drug of the dipeptidyl peptidase inhibitor class (Savage et al., 2009), and cyclopropa[c]quinolones of general structure 5 were discovered as antiviral drugs acting as HIV-1 non-nucleoside reverse transcriptase inhibitors (Luo et al., 2015; Pedroni et al., 2015; Truong et al., 2013; Saget and Cramer, 2012; Yong et al., 2007; Ellis et al., 2006; Bates et al., 1987). Furthermore, as highly strained three-membered rings, aziridines and cyclopropanes are very active species for ring-opening and ring-expansion reactions (Tummanapalli et al., 2014; Stankovic et al., 2012; Tang and Qin, 2012; Li et al., 2011; Ye and Yu, 2011; De Simone and Waser, 2009; Xu et al., 2008; Singh et al., 2007; Coldham and Hufton, 2005; Rotzoll et al., 2005; Kim et al., 2004; Reissig and Zimmer, 2003), thus providing access to a wide variety of multifunctional compounds. Our long standing interest in developing synthetic strategies for fused heterocyclic compounds (Marin-Luna et al., 2015; Alajarin et al., 2012; Alajarin et al., 2007; Alajarin et al., 2005; Molina et al., 1992a,b; Molina et al., 1991; Molina et al., 1990; Molina et al., 1989a,b; Molina et al., 1988) focused our attention to the tricyclic scaffolding present in the aziridino[2,3-c]quinolines 2 and the antiviral cyclopropa[c]quinolones 5.
Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-hydroxy-β-amino esters
2016, TetrahedronCitation Excerpt :The reaction mixture was then concentrated in vacuo and the residue was partitioned between CH2Cl2 (500 mL) and H2O (500 mL). The aqueous layer was extracted with CH2Cl2 (2×200 mL) and the combined organic extracts were then dried and concentrated in vacuo to give 82 as a yellow oil (12.6 g, 96%, >99:1 er);37 νmax (ATR) 3467 (N–H), 1325 (C–F); [α]D20 +39.4 (c 1.0 in CHCl3); δH (500 MHz, CDCl3) 1.30 (3H, d, J 6.6, C(α)Me), 1.55 (1H, br s, NH), 3.57 (1H, d, J 13.7, NCHAHBAr), 3.62 (1H, d, J 13.7, NCHAHBAr), 3.71 (1H, q, J 6.6, C(α)H), 7.16–7.29 (5H, m, Ph), 7.32 (2H, d, J 8.0, C(2)H, C(6)H), 7.48 (2H, d, J 8.0, C(3)H, C(5)H); δC (125 MHz, CDCl3) 24.5 (C(α)Me), 51.1 (NCH2Ar), 57.6 (C(α)), 124.3 (q, J 271.8, CF3), 125.3 (q, J 3.8, C(3), C(5)), 126.7 (m-Ph), 127.1 (p-Ph), 128.3 (o-Ph), 128.6 (C(2), C(6)), 129.1 (q, J 32,4, C(4)), 144.8 (C(1)), 145.3 (i-Ph); δF (377 MHz, CDCl3) −62.3 (CF3); m/z (ESI+) 280 ([M+H]+, 100%); HRMS (ESI+) C16H17F3N+ ([M+H]+) requires 280.1308; found 280.1303. p-(Trifluoromethyl)acetophenone 108 (2.00 g, 10.6 mmol) was added to a stirred solution of benzylamine (1.10 mL, 10.1 mmol) in EtOH (6.5 mL) and the resultant mixture was heated at reflux for 3 h.