Thermal [3+2] cycloaddition reaction of N-acyliminophenanthridinium betaine with allenoates: Facile access to phenanthridine-fused tetracyclic heterocycles

Letters in Organic Chemistry

Volumn 11, Issue 3, 2014, Pages 220-224

  Li, Zhen ^a   Yu, Hao ^a   Zhang, Lei ^a   Liu, Honglei ^a   Na, Risong ^a   Bian, Qinghua ^a   Wang, Min ^a   Guo, Hongchao ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

Author keywords

Allenoate; Azomethine imine; Cycloaddition; Heterocycle; Phenanthridine

Indexed keywords

EID: 84899927896     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178610666131120003018     Document Type: Article

References (50)

1. Schantl, J.G. In: Science of Synthesis; Padwa, A, Ed.; Georg Thieme Verlag: New York, 2004; Vol. 27, pp. 731-824.
2. Shintani, R.; Fu, G.C. A new copper-catalyzed [3+2] cycloaddition: Enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles. J. Am. Chem. Soc., 2003, 125, 10778-10779.
3. Chung, F.; Chauveau, A.; Seltki, M.; Bonin, M.; Micouin, L. Asymmetric 1,3- dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine. Tetrahedron Lett., 2004, 45, 3127-3130.
4. Pezdirc, L.; Jovanovski, V.; Bevk, D.; Jakše, R.; Pirc, S.; Meden, A.; Stanovnik, B.; Svete, J. Stereocontrol in cycloadditions of (1Z,4R*,5R*)- 1-arylmethylidene-4-benzoylamino-5-phenylpyrazolidin- 3-on-1- azomethine imines. Tetrahedron 2005, 61, 3977-3990.
5. Suárez, A.; Downey, C.W.; Fu, G.C. Kinetic resolutions of azomethine imines via copper-catalyzed [3+2] cycloadditions. J. Am. Chem. Soc., 2005, 127, 11244-11245.
6. Shintani, R.; Hayashi, T. Palladium- catalyzed [3+3] cycloaddition of trimethylenemethane with azomethine imines. J. Am. Chem. Soc., 2006, 128, 6330-6331.
7. Chen, W.; Yuan, X.-H.; Li, R.; Du, W.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with alpha,beta-unsaturated aldehydes. Adv. Synth. Catal., 2006, 348, 1818-1822.
8. Gergely, J.; Morgan, J.B.; Overman, L.E. Stereocontrolled synthesis of functionalized ciscyclopentapyrazolidines by 1,3-dipolar cycloaddition reactions of azomethine imines. J. Org. Chem., 2006, 71, 9144-9152.
9. Chan, A.; Scheidt, K.A. Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes. J. Am. Chem. Soc., 2007, 129, 5334-5335.
10. Suga, H.; Funyu, A.; Kakehi, A. Highly enantioselective and diastereoselective 1,3-dipolar cycloaddition reactions between azomethine imines and 3-acryloyl-2-oxazolidinone catalyzed by binaphthyldiimine- Ni(II) complexes. Org. Lett., 2007, 9, 97-100.
11. Pezdirc, L.; Cerkovnik, J.; Pirc, S.; Stanovnik, B.; Svete, J. Stereoselective cycloadditions of (1Z,4R*,5R*)-1-arylmethylidene-4- benzoylamino-5- phenylpyrazolidin-3-on-1-azomethine imines to maleimides. Tetrahedron, 2007, 63, 991-999.
12. Shintani, R.; Murakami, M.; Hayashi, T. Gamma-methylidene-delta- valerolactones as a coupling partner for cycloaddition: Palladium-catalyzed [4+3] cycloaddition with nitrones. J. Am. Chem. Soc., 2007, 129, 12356-12357.
13. Chen, W.; Du, W.; Duan, Y.-Z.; Wu, Y.; Yang, S.-Y.; Chen, Y.-C. Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: beneficial effects of hydrogen bonding. Angew. Chem., Int. Ed., 2007, 46, 7667-7670.
14. Sibi, M.P.; Rane, D.; Stanley, L.M.; Soeta, T. Copper (II)- catalyzed exo and enantioselective cycloadditions of azomethine imines. Org. Lett., 2008, 10, 2971-2974.
15. Perreault, C.; Goudreau, S.R.; Zimmer, L.E.; Charette, A.B. Cycloadditions of aromatic azomethine imines with 1,1-cyclopropane diesters. Org. Lett., 2008, 10, 689-692.
16. Shapiro, N.D.; Shi, Y.; Toste, F.D. Gold-catalyzed [3+3]-annulation of azomethine imines with propargyl esters. J. Am. Chem. Soc., 2009, 131, 11654-11655.
17. Keller, M.; Sido, A.S.S.; Pale, P.; Sommer, J. Copper (I) zeolites as heterogeneous and ligand-free catalysts: [3+2] cycloaddition of azomethine imines. Chem. Eur. J., 2009, 15, 2810-2817.
18. Hashimoto, T.; Maeda, Y.; Omote, M.; Nakatsu, H.; Maruoka, K. Catalytic enantioselective 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated aldehydes. J. Am. Chem. Soc., 2010, 132, 4076-4077.
19. Ogawa, S.; Nishimine, T.; Tokunaga, E.; Shibata, N. Expeditious synthesis of trifluoromethylated heterocycles: Noncatalytic 1,3-dipolar cyclization of azomethine imines with (alpha-trifluoromethyl)acrylates. Synthesis 2010, 19, 3274-3281.
20. Hashimoto, T.; Omote, M.; Maruoka, K. Asymmetric inverse-electron-demand 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: An Umpolung strategy. Angew. Chem. Int. Ed., 2011, 50, 3489-3492.
21. Hashimoto, T.; Omote, M.; Maruoka, K. Catalytic asymmetric alkynylation of C1- substituted C,N-Cyclic azomethine imines by CuI/chiral Brønsted acid Co-catalyst. Angew. Chem. Int. Ed., 2011, 50, 8952-8955.
22. Novak, A.; Bezenšek, J.; Pezdirc, L.; Grošelj, U.; Kasunič, M.; Podlipnik, Č.; Stanovnik, B.; Šimůnek, P.; Svete, J. Regio- and stereoselective cycloadditions of (1Z,4R*, 5R*)-1-arylmethylidene- 4-benzoylamino-3-oxo-5-phenylpyrazolidin-1-ium-2- ides to methyl methacrylate. Tetrahedron 2011, 67, 9729-9735.
23. Yoshimura, K.; Oishi, T.; Yamaguchi, K.; Mizuno, N. An efficient, ligand-Free, heterogeneous supported copper hydroxide catalyst for the synthesis of N,N-bicyclic pyrazolidinone derivatives. Chem. Eur. J., 2011, 17, 3827-3831.
24. Kawai, H.; Yuan, Z.; Tokunaga, E.; Shibata, N. Regioselective synthesis of pyrazole triflones based on triflyl alkyne cycloadditions. Org. Lett., 2012, 14, 5330-5333.
25. Imaizumi, T.; Yamashita, Y.; Kobayashi, S. Group 11 metal amidecatalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes. J. Am. Chem. Soc., 2012, 134, 20049-20052.
26. Soeta, T.; Tamura, K.; Ukaji, Y. [5 + 1] Cycloaddition of C,Ncyclic N'-acyl azomethine imines with isocyanides. Org. Lett., 2012, 14, 1226-1229.
27. Xu, X.; Qian, Y.; Zavalij, P. Y.; Doyle, M.P. Highly Selective catalyst-dependent competitive 1,2-C→C, -O→C, and -N→C migrations from β-Methylene-β-silyloxy-β- amido-α-diazoacetates. J. Am. Chem. Soc., 2013, 135, 1244-1247.
28. Na, R.; Jing, C.; Xu, Q.; Jiang, H.; Wu, X.; Shi, J.; Zhong, J.; Wang, M.; Benitez, D.; Tkatchouk, E.; Goddard, W.A., III; Guo, H.; Kwon, O. Phosphine-catalyzed annulations of azomethine imines: allene-dependent [3+2], [3+3], [4+3], and [3+2+3] pathways. J. Am. Chem. Soc., 2011, 133, 13337.
29. Liu, J.; Liu, H.; Na, R.; Wang, G.; Li, Z.; Yu, H.; Wang, M.; Zhong, J.; Guo, H. Phosphine-catalyzed [3+2] and [3+3] annulations of azomethine imines with ethyl 2-butynoate. Chem. Lett., 2012, 41, 218.
30. Jiang, H.; Na, R.; Zhang, L.; Liu, H.; Li, Z.; Wang, B.; Guo, H.C. Samarium diiodide mediated highly diastereoselective conjugate reduction of the alpha,beta-unsaturated ester moiety in heterocyclic compounds. Synthesis, 2012, 44, 3633-3638.
31. Jing, C.; Na, R.; Wang, B.; Liu, H.; Zhang, L.; Liu, J.; Wang, M.; Zhong, J.; Kwon, O.; Guo, H. Phosphine-catalyzed [3+2] and [4+3] annulation reactions of C,N-cyclic azomethine imines with allenoates. Adv. Synth. Catal., 2012, 354, 1023.
32. Na, R.; Liu, H.; Li, Z.; Wang, B.; Liu, J.; Wang, M.-A.; Wang, M.; Zhong, J.; Guo, H. Thermal [3+2] cycloaddition reaction of azomethine imines with allenoates for dinitrogen-fused heterocycles. Tetrahedron 2012, 68, 2349-2356.
33. Zhang, L.; Jing, C.; Liu, H.; Wang, B.; Li, Z.; Jiang, H.; Yu, H.; Guo, H. Thermal [3+2] cycloaddition of aromatic azomethine imines with allenoates. Synthesis, 2013, 45, 53-64.
34. Wu, X.; Na, R.; Liu, H.; Liu, J.; Wang, M.; Zhong, J.; Guo, H. Sequential [3+2] cycloaddition/rearrangement reaction of imidazolone nitrones and allenoates for the efficient synthesis of functionalized imidazolidinone. Tetrahedron Lett., 2012, 53, 342-344.
35. Inbar-Rozensal, D.; Castiel, A.; Visochek, L.; Castel, D.; Dantzer, F.; Izraeli, S.; Cohen-Armon, M. A selective eradication of human nonhereditary breast cancer cells by phenanthridinederived polyADP-ribose polymerase inhibitors. Breast Cancer Res., 2009, 11, R78-R78.
36. Lu, T.; Guo, C.; Ni, P. Design, synthesis and evaluation of phenanthridine derivatives interacting with Gquadruplex as telomerase. J. China Pharm. Univ., 2004, 35, 99-105.
37. Rajagopalan, R.; Lin, T.; Karwa, A.S.; Poreddy, A.R.; Asmelash, B.; Dorshow, R.B. Type 1 phototherapeutic agents. 2. Cancer cell viability and ESR studies of tricyclic diarylamines. ACS Med. Chem. Lett., 2012, 3, 284-288.
38. Cappoen, D.; Jacobs, J.; Tuyen, N. V.; Claessens, S.; Diels, G.; Anthonissen, R.; Einarsdottir, T.; Fauville, M.; Verschaeve, L.; Huygen, K.; De Kimpe, N. Straightforward palladium-mediated synthesis and biological evaluation of benzo[j]phenanthridine-7,12-diones as anti-tuberculosis agents. Eur. J. Med. Chem., 2012, 48, 57-68.
39. Tohyama, S.; Choshi, T.; Matsumoto, K.; Yamabuki, A.; Hieda, Y.; Nobuhiro, J.; Hibino, S. Total synthesis of bioactive indolo[3,2-j] phenanthridine alkaloid, Calothrixin B. Heterocycles 2010, 82, 397-416.
40. Caballero-George, C.; Vanderheyden, P. M. L.; Apers, S.; Van den Heuvel, H.; Solis, P. N.; Gupta, M. P.; Claeys, M.; Pieters, L.; Vauquelin, G.; Vlietinck, A. J. Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: Bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens. Planta Med., 2002, 68, 770-775.
41. Ramkumar N.; Nagarajan R. Total synthesis of Calothrixin A and B via C-H activation. J. Org. Chem., 2013, 78, 2802-2807.
42. Godtfredsen, W.O.; Vangedal, S. The reaction of hydrazine with cinnamic acid derivatives. Acta Chem. Scand., 1955, 9, 1498-1509.
43. Huisgen, R.; Grashey, R.; Laur, P.; Leitermann, H. 1.3- Dipolare additionen der azomethin-imine. Angew. Chem., 1960, 72, 416-417.
44. Dorn, H.; Otto, A. Reaction of pyrazolid-3-one with carbonyl compounds. Chem. Ber., 1968, 101, 3287-3301.
45. Dorn, H.; Otto, A. Syntheses by means of 1-alkylidene- and 1-(arylalkylidene)- 3-pyrazolidone N,N-betaines, a new type of stable azomethine imine. Angew. Chem., Int. Ed. Engl., 1968, 7, 214-215.
46. Tamura, Y.; Miki, Y.; Nishikawa, Y.; Ikeda, M. 1,3-Dipolar cycloaddition reaction of phenanthridinium N-imines and Nbenzoylimine with acetylenic-compounds. J. Heterocycl. Chem., 1976, 13, 317-320.
47. Tamura, Y.; Minamikawa, J.; Miki, Y.; Matsugashita, S.; Ikeda, M. Novel method for heteroaromatic Nimines. Tetrahedron Lett., 1972, 13, 4133-4135.
48. Carpino, L.A. o-Acylhydroxylamines. II. o-Mesitylenesulfonyl- hydroxylamine, opara- toluenesulfonyl-hydroxylamine and o-mesitoylhydroxylzmine. J. Am. Chem. Soc., 1960, 82, 3133-3135.
49. Agai, B.; Lempert, K. Isoquinolinium amidates-synthesis and some reactions of N-acyl and N-sulfonyl derivatives. Tetrahedron, 1972, 28, 2069-2084.
50. Crystallographic data for 4be has been deposited with the Cambridge Crystallographic Data Centre as deposition number CCDC 940071. These data can be obtained free of charge via www.ccdc.cam. ac.uk/data-request/cif, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.