Efficient synthesis of phenanthridinone derivatives via a palladium-catalyzed coupling process

Organic Letters

Volumn 9, Issue 2, 2007, Pages 183-186

  Furuta, Takumi ^a   Kitamura, Yuki ^a   Hashimoto, Ayano ^a   Fujii, Satoshi ^a   Tanaka, Kiyoshi ^a   Kan, Toshiyuki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; LIGAND; PALLADIUM; PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETATES; CATALYSIS; LIGANDS; MOLECULAR STRUCTURE; PALLADIUM; PHENANTHRENES; STEREOISOMERISM;

EID: 33846641693     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062599z     Document Type: Article

References (19)

1. For reviews on Pd-catalyzed C-N bond formations, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
2. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
3. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
4. (d) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
5. (a) Yoshikawa, S.; Odaira, J.; Kitamura, Y.; Bedekar, A. V.; Furuta, T.; Tanaka, K. Tetrahedron 2004, 60, 2225-2234.
6. (b) Kitamura, Y.; Hashimoto, A.; Yoshikawa, S.; Odaira, J.; Furuta, T.; Kan, T.; Tanaka, K. Synlett 2006, 115-117.
7. Phenanthridinone derivatives are often found in bioactive compounds and have received much attention as valuable intermediates for nitrogen-containing natural products. See: (a) Harayama, T.; Akamatsu, H.; Okamura, K.; Miyagoe, T.; Akiyama, T.; Abe, H.; Takeuchi, Y. J. Chem. Soc. Perkin Trans. 1 2001, 523-528.
8. (b) Harayama, T.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002, 237-241.
9. (c) Bellocchi, D.; Macchiarulo, A.; Costantino, G.; Pellicciari, R. Bioorg. Med. Chem. 2005, 13, 1151-1157.
10. (d) Ishida, J.; Hattori, K.; Yamamoto, H.; Iwashita, A.; Mihara, K.; Matsuoka, N. Bioorg. Med. Chem. Lett. 2005, 15, 4221-4225.
11. 4, and evaporated. The residue was purified by column chromatography on silica gel (hexane/AcOEt, 7:3) to afford 12 (19 mg, 77%) as a colorless solid. The structure of 12 was unambiguously determined by X-ray analysis. (See Supporting Information.)
12. The reaction did not proceed unless the amide nitrogen group was protected. Only the starting material was recovered. The same observation is depicted in ref 6.
13. Ferraccioli, R.; Carenzi, D.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2006, 128, 722-723.
14. A similar reaction was originally discovered by Caddick et al. during their investigations of an intramolecular Heck reaction of 13b in the presence of an N-heterocyclic carbene (NHC) ligand. Phenanthridinone 14b was obtained in 32% yield. See: Caddick, S.; Kofie, W. Tetrahedron Lett. 2002, 43, 9347-9350.
15. 2.
16. During the reaction of 11 to 12 (Table 1, entry 1), we observed a peak that corresponds to benzyl isocyanate (m/z 313) using GC-MS analysis. For details of the GC-MS analysis, see Supporting Information. Moreover, symmetrical urea derivative 25 was isolated in 40% yield from the experiment of entry 4 in Table 2. Urea 25 could be derived from the dimerization and subsequent decarboxylation of corresponding isocyanate derivative 26.
17. The reason for the predominant yield of homocoupling products 16d and 16g might be explained by the reactivity order of the substrates.
18. The predominant formation of N-benzyl-substituted phenanthridinone derivative 16d could be explained by the high reactivity of N-benzyl-protected substrate 15d.
19. The reaction with N-tethered 2-bromobenzamide 27 gave phenanthridinone dimer 28 as the major product. For the details of this reaction, see Supporting Information. (Chemical Equation Presented)