Synthesis of (Z)-2-[(Z)-3-alkylideneisobenzofuran-1(3H)-ylidene]acetic acid derivatives by sequential coupling-cyclization between 3-(2-iodophenyl)-3- oxopropanoic acid derivatives and terminal alkynes

Synthesis

Volumn , Issue 7, 2008, Pages 1094-1098

  Kobayashi, Kazuhiro ^a   Hashimoto, Kenichi ^a   Fukamachi, Shuhei ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

Alkynes; Coupling; Furans; Palladium; Ring closure

Indexed keywords

ALKYNES; FURANS; RING CLOSURES; ROOM TEMPERATURE;

ACETIC ACID; CYCLIZATION; DERIVATIVES; MOLAR MASS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

FURAN RESINS;

2 (3 ALKYLIDENEISOBENZOFURAN 1 YLIDENE)ACETIC ACID DERIVATIVE; 3 (2 IODOPHENYL) 3 OXOPROPANOIC ACID DERIVATIVE; ACETIC ACID DERIVATIVE; ALKYNE DERIVATIVE; BIS(TRIPHENYLPHOSPHINE)PALLADIUM; COPPER; IODIDE; N,N DIMETHYLFORMAMIDE; PALLADIUM; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 42049083111     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032120     Document Type: Article

References (18)

1. (a) Kobayashi, K.; Uneda, T.; Kawakita, M.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 1997, 38, 837.
2. (b) Chaplin, J. H.; Flynn, B. L. Chem. Commun. 2001, 1594.
3. (c) Kabalka, G. W.; Wang, L.; Pagni, R. M. Tetrahedron 2001, 57, 8017.
4. (d) Bossharth, E.; Desbordes, P.; Monteiro, M.; Balme, G. Org. Lett. 2003, 5, 2441.
5. (e) Sakai, N.; Annaka, K.; Konakahara, T. Org. Lett. 2004, 6, 1527.
6. (a) Zamilpa, A.; Herrera-Ruiz, M.; del Olmo, E.; Lóez- Pérez, J. L.; Tortoriello, J.; San Feliciano, A. Bioorg. Med. Chem. Lett. 2005, 15, 3483.
7. (b) Bedoya, L. M.; del Olmo, E.; Sancho, R.; Barboza, B.; Beltrán, M.; García-Cadenas, A. E.; Sánchez-Palomino, S.; López-Pérez, J. L.; Muñoz, E.; San Feliciano, A.; Alcamí, J. Bioorg. Med. Chem. Lett. 2006, 16, 4075.
8. (a) Lee, K. Y.; Kim, J. M.; Kim, J. N. Synlett 2003, 357.
9. (b) Kapoor, M.; Dhawan, S. N.; Mor, S.; Bhatia, S. C.; Gupta, S. C.; Hundal, M. S. Tetrahedron 2003, 59, 5027.
10. (c) Albrecht, U.; Nguyen, V. T. H.; Langer, P. Synthesis 2006, 1111.
11. (d) Mor, S.; Dhawan, S. N.; Kapoor, M.; Kumar, D. Tetrahedron 2007, 63, 594.
12. (e) Coelho, F.; Veronese, D.; Pavam, C. H.; de Paula, V. I.; Buffon, R. Tetrahedron 2006, 62, 4563.
13. (f) Duchene, A.; Thibonnet, J.; Parrain, J. L.; Anselmi, E.; Abarbri, M. Synthesis 2007, 597.
14. (g) Kanazawa, C.; Terada, M. Tetrahedron Lett. 2007, 48, 933.
15. (h) For reports on the synthesis by the coupling-cyclization sequence between o-halobenzoic acids and terminal alkynes, see: Subramanian, V.; Batchu, V. R.; Barange, D.; Pal, M. J. Org. Chem. 2005, 70, 4778; and pertinent references cited in these papers.
16. Kundu, N. G.; Pal, M.; Mahanty, J. S.; Dasgupta, S. J. Chem. Soc., Chem. Commun. 1992, 41.
17. Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonahara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517.
18. Torregrosa, J. L.; Baboulene, M.; Speziale, V.; Lattes, A. Tetrahedron 1983, 39, 3101.