Mild and efficient syntheses of 1-aryl-3,4-dihydroisoquinolines and 1-aryl-3,4-dihydro-β-carbolines via regiospecific β-eliminations of the corresponding N-tosyl-1,2,3,4-tetrahydroisoquinolines and N-tosyl-1,2,3,4-tetrahydro-β-carbolines

Synthetic Communications

Volumn 42, Issue 19, 2012, Pages 2806-2817

  Dong, Jing ^a   Shi, Xiao Xin ^a   Xing, Jing ^a   Yan, Jing Jing ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

1,2,3,4 tetrahydro carboline; 1,2,3,4 tetrahydroisoquinoline; 3,4 Dihydro carboline; 3,4 Dihydroisoquinoline; Synthesis

Indexed keywords

BETA CARBOLINE DERIVATIVE; DIMETHYL SULFOXIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM HYDROXIDE; SODIUM HYDROXIDE; SOLVENT; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; QUANTUM YIELD; SYNTHESIS; TEMPERATURE;

EID: 84861971736     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.568659     Document Type: Article

References (39)

1. (a) Christopher, J. A.; Atkinson, F. L.; Bax, B. D.; Brown, M. J. B.; Champigny, A. C.; Chuang, T. T.; Jones, E. J.; Mosley, J. E.; Musgrave, J. R. 1-Aryl-3,4-dihydroisoquinoline inhibitors of JNK3. Bioorg. Med. Chem. Lett. 2009, 19, 2230-2234;
2. (b) Batra, S.; Sabnis, Y. A.; Rosenthal, P. J.; Avery, M. A. Structure-based approach to falcipain-2 inhibitors: synthesis and biological evaluation of 1,6,7-trisubstituted dihydroisoquinolines and isoquinolines. Bioorg. Med. Chem. 2003, 11, 2293-2299;
3. (c) Bermejo, A.; Andreu, I.; Suvire, F.; Leonce, S.; Caignard, D. H.; Renard, P.; Pierre, A.; Enriz, R. D.; Cortes, D.; Cabedo, N. Syntheses and antitumor targeting G1 phase of the cell cycle of benzoyldihydroisoquinolines and related 1-substituted isoquinolines. J. Med. Chem. 2002, 45, 5058-5068. (Pubitemid 35278702)
4. (a) Shen, Y.-C.; Chen, C.-Y.; Hsieh, P.-W.; Duh, C.-Y.; Lin, Y.-M.; Ko, C.-L. The preparation and evaluation of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carboline derivatives as potential antitumor agents. Chem. Pharm. Bull. 2005, 53, 32-36;
5. (b) Lee, Y.-J.; Han, Y.-R.; Park, W.; Nam, S.-H.; Oh, K.-B.; Lee, H.-S. Synthetic analogs of indole-containing natural products as inhibitors of sortase A and isocitrate lyase. Bioorg. Med. Chem. Lett. 2010, 20, 6882-6885;
6. (c) Rommelspacher, H.; Bruening, G.; Susilo, R.; Nick, M.; Hill, R. Pharmacology of harmalan (1-methyl-3,4-dihydro-β-carboline). Eur. J. Pharmacol. 1985, 109, 363-371.
7. (a) Chrzanowska, M.; Rozwadowska, M. D. Asymmetric synthesis of isoquinoline alkaloids. Chem. Rev. 2004, 104, 3341-3370;
8. (b) Noyori, R.; Hashiguchi, S. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc. Chem. Res. 1997, 30, 97-102;
9. (c) Evanno, L.; Ormala, J.; Pihko, P. M. A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple Noyori-type catalysts in aqueous media. Chem. Eur. J. 2009, 15, 12963-12967;
10. (d) Li, C.; Xiao, J. Asymmetric hydrogenation of cyclic imines with an ionic Cp*Rh(III) catalyst. J. Am. Chem. Soc. 2008, 130, 13208-13209;
11. (e) Hajipour, A. R.; Hantehzadeh, M. Asymmetric reduction of prochiral cyclic imines to alkaloid derivatives by novel asymmetric reducing reagent in THF or under solid-state conditions. J. Org. Chem. 1999, 64, 8475-8478. (Pubitemid 129599340)
12. (a) da Silva, W. A.; Rodrigues, M. T.; Shankaraiah, N.; Ferreira, R. B.; Andrade, C. K. Z.; Pilli, R. A.; Santos, L. S. Novel supramolecular palladium catalyst for the asymmetric reduction of imines in aqueous media. Org. Lett. 2009, 11, 3238-3241;
13. (b) Espinoza-Moraga, M.; Petta, T.; Vasquez-Vasquez, M.; Laurie, V. F.; Moraes, L. A. B.; Santos, L. S. Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus. Tetrahedron: Asymmetry 2010, 21, 1988-1992;
14. (c) Santos, L. S.; Fernandes, S. A.; Pilli, R. A.; Marsaioli, A. J. A novel asymmetric reduction of dihydro-β-carboline derivatives using calix[6]arene/chiral amine as a host complex. Tetrahedron: Asymmetry 2003, 14, 2515-2519. (Pubitemid 37093869)
15. (a) Martin, N. H.; Champion, S. L.; Belt, P. B. Regiospecific oxidation of substituted 1-benzyl-3,4-dihydro-isoquinolines using singlet oxygen. Tetrahedron Lett. 1980, 21, 2613-2616;
16. (b) Capilla, A. S.; Romero, M.; Pujol, M. D.; Caignard, D. H.; Renard, P. Synthesis of isoquinolines and tetrahydroisoquinolines as potential antitumor agents. Tetrahedron 2001, 57, 8297-8303. (Pubitemid 32885648)
17. (a) Ivanov, I.; Nikolova, S.; Statkova-Abeghe, S. A simple method for the synthesis of 1-substituted β-carboline derivatives from tryptamine and carboxylic acids in polyphosphoric acid. Heterocycles 2005, 65, 2483-2492;
18. (b) Garcia, M. D.; Wilson, A. J.; Emmerson, D. P. G.; Jenkins, P. R. Regioselective photo-oxidation of 1-benzyl-4,9-dihydro-3H-β-carbolines. Chem. Commun. 2006, 2586-2588;
19. (c) Radchenko, O. S.; Novikov, V. L.; Elyakov, G. B. A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds. Tetrahedron Lett. 1997, 38, 5339-5342. (Pubitemid 27300196)
20. (a) Bischler, A.; Napieralski, B. A new method for the synthesis of isoquinolines. Ber. 1893, 26, 1903-1908;
21. (b) Whaley, W. M.; Govindachari, T. R. Preparation of 3,4-dihydroisoquinolines and related compounds by Bischler-Napieralski reaction. Org. React. 1951, 6, 74-150;
22. (c) Fodor, G.; Nagubandi, S. Correlation of the von Braun, Ritter, Bischler-Napieralski, Beckmann, and Schmidt reactions via nitrilium salt intermediates. Tetrahedron 1980, 36, 1279-1300;
23. (d) Saito, T.; Yoshida, M.; Ishikawa, T. Triphosgene: A versatile reagent for Bischler-Napieralski reaction. Heterocycles 2001, 54, 437-438;
24. (e) Hegedues, A.; Hell, Z.; Potor, A. A new, environmentally friendly method for the Bischler-Napieralski cyclization using zeolite catalyst. Catal. Commun. 2006, 7, 1022-1024, and the references cited therein; (Pubitemid 44585261)
25. (f) Movassaghi, M.; Hill, M. D. A versatile cyclodehydration reaction for the synthesis of isoquinoline and β-carboline derivatives. Org. Lett. 2008, 10, 3485-3488.
26. (a) Okimoto, M.; Takahashi, Y.; Numata, K.; Sasaki, G. Electrochemical dehydrogenation of 1,2,3,4-tetrahydroisoquinoline to 3,4-dihydroisoquinoline. Heterocycles 2005, 65, 371-375;
27. (b) Murahashi, S.-I.; Okano, Y.; Sato, H.; Nakae, T.; Komiya, N. Aerobic ruthenium-catalyzed oxidative transformation of secondary amines to imines. Synlett 2007, 1675-1678;
28. (c) Misztal, S.; Cegla, M. Selective and efficient synthesis of 3,4-dihydro-β- carboline derivatives. Synthesis 1985, 1134-1135.
29. Ito, K.; Tanaka, H. Syntheses of 1,2,3,4-tetrahydroisoquinolines from N-sulfonylphenethylamines and aldehydes. Chem. Pharm. Bull. 1977, 25, 1732-1739.
30. 2B) contractile receptor in the rat stomach fundus. J. Med. Chem. 1996, 39, 2773-2780.
31. Ishikawa, T.; Manabe, S.; Aikawa, T.; Kudo, T.; Saito, S. Intramolecular catalytic Friedel-Crafts reactions with allenyl cations for the synthesis of quinolines and their analogues. Org. Lett. 2004, 6, 2361-2364. (Pubitemid 38952540)
32. Dong, J.; Shi, X.-X.; Yan, J.-J.; Xing, J.; Zhang, Q.; Xiao, S. Efficient and practical onepot conversions of N-tosyltetrahydroisoquinolines into isoquinolines and of N-tosyltetrahydro- β-carbolines into β-carbolines through tandem β-elimination and aromatization. Eur. J. Org. Chem. 2010, 6987-6992.
33. Van Binst, G.; Baert, R.; Biesemans, M.; Mortelmans, C.; Salsmans, R. Benzo- and indoloquinolizine derivatives. VII. The dehydrogenation of enamines in the synthesis of benzo[c]substituted quinolizidines. Bull. Soc. Chim. Belg. 1976, 85, 1-9.
34. Yang, J.; Hua, W.-Y.; Wang, F.-X.; Wang, Z.-Y.; Wang, X. Design, synthesis, and inhibition of platelet aggregation for some 1-o-chlorophenyl-1,2, 3,4-tetrahydroisoquinoline derivatives. Bioorg. Med. Chem. 2004, 12, 6547-6557. (Pubitemid 39535177)
35. Lantos, I.; Bhattacharjee, D.; Eggleston, D. S. Synthesis of 1-phenyl-5H-2-benzazepines by ring expansion of 1-phenyl-1,2- dihydroisoquinolines. J. Org. Chem. 1986, 51, 4147-4150. (Pubitemid 17202249)
36. Doi, S.; Shirai, N.; Sato, Y. Abnormal products in the Bischler-Napieralski isoquinoline synthesis. J. Chem. Soc., Perkin Trans. 1 1997, 2217-2221. (Pubitemid 127781392)
37. Neuvonen, K.; Fueloep, F.; Neuvonen, H.; Koch, A.; Kleinpeter, E.; Pihlaja, K. Propagation of polar substituent effects in 1-(substituted phenyl)-6,7-dimethoxy-3,4-dihydroand -1,2,3,4-tetrahydroisoquinolines as explained by resonance polarization concept. J. Org. Chem. 2005, 70, 10670-10678. (Pubitemid 43041073)
38. Yamada, K.; Takeda, M.; Iwakuma, T. Asymmetric reduction of cyclic imines with chiral sodium acyloxyborohydrides. J. Chem. Soc., Perkin Trans. 1 1983, 265-270.
39. Mohsen, A.; Omar, M. E.; Yamada, S. Studies on thioamides. IV. Extension of the cyclodesulfurization reaction to synthesize 1-substituted and 1,3-disubstituted-3,4-dihydro-9Hpyrido[ 3,4-b]indole derivatives. Chem. Pharm. Bull. 1966, 14, 856-861.