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 2018; 50(11): 2181-2190
DOI: 10.1055/s-0037-1609153
DOI: 10.1055/s-0037-1609153
paper
Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine
We gratefully acknowledge the financial support from the National Research, Development and Innovation Office (K-116150). We are also grateful for the financial support from Soneas Research Ltd.Further Information
Publication History
Received: 08 December 2017
Accepted: 15 December 2017
Publication Date:
07 March 2018 (online)
Abstract
A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products.
Key words
isoquinoline - regioexhaustive - cross-coupling - heterocycles - fused-ring systems - ellipticineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609153.
- Supporting Information
-
References
- 1a Bentley KW. The Isoquinoline Alkaloids . Harwood Academic Publishers; Amsterdam: 1998
- 1b Eicher T. Hauptmann S. Speicher A. The Chemistry of Heterocycles . Wiley-VCH; Weinheim: 2003
- 1c Bentley KW. Nat. Prod. Rep. 2006; 23: 444
- 1d Joule JA. Mills K. Heterocyclic Chemistry . Wiley-Blackwell; West Sussex: 2010. 5th ed.
- 1e Vitaku E. Smith DT. Njardarson JT. J. Med. Chem. 2014; 57: 10257
- 1f Iranshahy M. Quinn RJ. Iranshahi M. RSC Adv. 2014; 4: 15900
- 1g Chrzanowska M. Grajewska A. Rozwadowska MD. Chem. Rev. 2016; 116: 12369
- 2a Pomeranz C. Monatsh. Chem. 1893; 14: 116
- 2b Fritsch P. Ber. Dtsch. Chem. Ges. 1893; 26: 419
- 2c Pictet A. Spengler T. Ber. Dtsch. Chem. Ges. 1911; 44: 2030
- 2d Bischler A. Napieralski B. Ber. Dtsch. Chem. Ges. 1893; 26: 1903
- 2e For a recent diversity-oriented approach, see: Awuah E. Capretta A. J. Org. Chem. 2010; 75: 5627
- 3a Roesch KR. Larock RC. J. Org. Chem. 1998; 63: 5306
- 3b Guimond N. Fagnou K. J. Am. Chem. Soc. 2009; 131: 12050
- 3c Gerfaud T. Neuville L. Zhu J. Angew. Chem. Int. Ed. 2009; 48: 572
- 3d Shi Z. Koester DC. Boultadakis-Arapinis M. Glorius F. J. Am. Chem. Soc. 2013; 135: 12204
- 3e Jiang H. Yang J. Tang X. Wu W. J. Org. Chem. 2016; 81: 2053
- 3f Chu H. Xue P. Yu J.-T. Cheng J. J. Org. Chem. 2016; 81: 8009
- 3g Kuai C. Wang L. Li B. Yang Z. Cui X. Org. Lett. 2017; 19: 2102
- 4a Schlosser M. Angew. Chem. Int. Ed. 2005; 44: 376
- 4b Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
- 5 Grethe G. The Chemistry of Heterocyclic Compounds, Isoquinolines. John Wiley & Sons; New York: 1981
- 6 Fortner P. Monatsh. Chem. 1893; 14: 146
- 7 Gordon M. Pearson DE. J. Org. Chem. 1964; 29: 329
- 8 Brown WD. Gouliaev AH. Synthesis 2002; 83
- 9 Walker MD. Andrews BI. Burton AJ. Humphreys LD. Kelly G. Schilling MB. Scott PW. Org. Process Res. Dev. 2010; 14: 108
- 10 Tilstam U. Weinmann H. Org. Process Res. Dev. 2002; 6: 384
- 11a Keilin B. Cass WE. J. Am. Chem. Soc. 1942; 64: 2442
- 11b Graulich A. Scuvée-Moreau J. Seutin V. Liégeois J.-F. J. Med. Chem. 2005; 48: 4972
- 12a Tscherniac J. German Patent 134979, 1901
- 12b Einhorn A. Bischkopff E. Szelinski B. Schupp G. Spröngerts E. Ladisch C. Mauermayer T. Liebigs Ann. Chem. 1905; 343: 207
- 13 According to the literature,9 the benzene ring of 5,8-dichloroisoquinoline can be oxidized to give the appropriate pyridine-3,4-dicarboxylic acid.
- 14a Rossini AF. C. Muraca AC. A. Casagrande GA. Raminelli C. J. Org. Chem. 2015; 80: 10033
- 14b Ku AF. Cuny GD. Org. Lett. 2015; 17: 1134
- 14c Chen J. Wan M. Hua J. Sun Y. Lv Z. Li W. Liu L. Org. Biomol. Chem. 2015; 13: 11561
- 15a Miller RB. Moock T. Tetrahedron Lett. 1980; 21: 3319
- 15b Miller RB. Dugar S. Epperson JR. Heterocycles 1987; 25: 217
- 15c Nagao Y. Endo R. Tokumaru M. Arimitsu K. Heterocycles 2009; 77: 1403
- 15d Nagao Y. Hirota K. Tokumaru M. Kozawa K. Heterocycles 2007; 73: 593
- 15e Liu C.-Y. Knochel P. J. Org. Chem. 2007; 72: 7106
- 16 Godard A. Rocca P. Pomel V. Thomas-dit-Dumont L. Rovera JC. Thaburet JF. Marsais F. Quéguiner G. J. Organomet. Chem. 1996; 517: 25
- 17a Sam J. Shafik RM. Aparajithan K. J. Pharm. Sci. 1970; 59: 59
- 17b Wieting MJ. Fisher JT. Schafer GA. Visco DM. Gallucci CJ. Mattson EA. Eur. J. Org. Chem. 2015; 525
For pioneering work, see:
For recent examples, see: