A convenient approach to the synthesis of dialkyl 5-oxo-1,2-dihydro-5H- chromeno [4,3-b]pyridine-2,3-dicarboxylates

Synthetic Communications

Volumn 38, Issue 10, 2008, Pages 1579-1588

  Glasnov, Toma N ^a   Ivanov, Ivo C ^a  

^a MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

Annelated ring system; Coumarin; Enaminoaldehydes; Wittig reaction

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; CARBOXYLIC ACID; COUMARIN; DIETHYL 1 ALLYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIETHYL 1 BENZYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIETHYL 5 OXO 1 PROPYL 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIETHYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIETHYL ACETYLENEDICARBOXYLIC ACID DERIVATIVE; DIETHYL ETHYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIETHYL METHYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 1 ALLYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 1 BENZYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 1 BUTYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 1 ETHYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 1 METHYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 5 OXO 1 PROPYL 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; DIMETHYL 5 OXO 1,2 DIHYDRO 5H CHROMENO(4,3 B)PYRIDINE 2,3 DICARBOXYLATE; TRIPHENYLPHOSPHINE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOLATION PROCEDURE; WITTIG REACTION;

EID: 42549118954     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801929465     Document Type: Article

References (37)

1. (a) Ukawa, K.; Ishiguro, T.; Wada, Y.; Nohara, A. Synthesis of 5-oxo-5H-[1]benzopyrano[4,3-b]pyridine derivatives. Heterocycles 1986, 24, 1931-1941;
2. (b) Sun, W.; Cama, L. D.; Birzin, E. T.; Warrier, S.; Locco, L.; Mosley, R.; Hammond, M. L.; Rohrer, S. P. 6H-Benzo[c]chromene-6-one derivatives as selective ERβ agonists. Bioorg. Med. Chem. Lett. 2006, 16, 1468-1472;
3. (c) Pave, G.; Charald, P.; Viauld-Massuard, M.-C.; Troin, Y.; Guillaumet, G. New efficient synthesis of pyrido[2,3-c] and pyrido[3,2-c]coumarin derivatives. Synlett 2003, 987-990;
4. (d) Lewis, W. H.; Stonard, R. J.; Porras-Reyes, A. T.; Mustoe, T. A.; Thoms, A. Wound-healing composition. US Patent 5156847, 1992; Chem. Abstr. 1992, 117, 245630t;
5. (e) Connor, D. T.; Unangst, P. C.; Schwender, C. F.; Sorensen, R. J.; Carethers, M. E.; Puchalski, C.; Brown, R. E.; Finkel, M. P. 3-(Aminoalkyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c] pyridine-5-ones as potential anticholinergic bronchodilators. J. Med. Chem. 1989, 32, 683-688.
6. (a) Heber, D. 5H-[1]benzopyrano[4,3-b]pyridine by condensation of 3-acylchromones with enamines. Synthesis 1978, 691-692;
7. (b) Heber, D. Reactions of heterocycles containing the 2-acyl-2-propenone structure, II: Pyrido[2,3-d]pyrimidines from 4-oxo-4H-chromene-3-carbaldehydes and 4-aminouracils. Arch. Pharm. 1983, 316, 55-62;
8. (c) Heber, D. Reactions of heterocycles containing the 2-acyl-2-propenone structure, III: Pyrido[3,2-c]-coumarins from 3-substituted 1-benzopyrans and enamines. Arch. Pharm. 1987, 320, 402-406;
9. (d) Heber, D. Reactions of heterocycles containing the 2-acyl-2-propenone structure, V: [1]Benzopyrano[4,3-b]pyridine-2,5-(2H,5H)-diones by cyclisation of 3-substituted 4-aminocoumarins. Arch. Pharm. 1987, 320, 577-581;
10. (e) Heber, D. Reactions of heterocycles containing the 2-acyl-2-propenone structure, VI: Novel preparation of 6-oxo-6H-[1]benzopyrano[4,3-b]quinoline derivatives. Arch. Pharm. 1987, 320, 595-599;
11. (f ) Heber, D.; Berghaus, T. Synthesis of 5H-[1]benzopyrano[4,3-b] pyridine-5-ones containing an azacannabinoidal structure. J. Het. Chem. 1994, 31, 1353-1359;
12. 6a,10a-Tetrahydrocannabinol and heterocyclic analogs containing side chains. J. Med. Chem. 1976, 19, 461-471.
13. Wolfbeis, O. S. Luminescent heterocycles, part 8: Synthesis and properties of new hydoxy-substituted coumarin-derived laser dyes. Monats. Chem. 1978, 109, 1413-1421.
14. Razdan, R. J. The total synthesis of cannabinoids. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley and Sons: New York; 1981, Vol. 4, pp. 186-262.
15. (a) Majumdar, K. C.; Bhattacharyya, T. Synthesis of bioactive heterocycles: Amino Claisen rearrangement of 4-N-(4-aryloxybut-2ynyl)-N- methylaminocoumarins. Tetrahedron Lett. 2001, 42, 4231-4233;
16. (b) Chatterjea, J. N.; Shaw, S. C.; Singh, J. N.; Singh, S. N. Synthesis of condensed pyridines, part I: Pyrido[3,2-c]coumarins. Ind. J. Chem. Sec. B 1977, 15, 430-431;
17. (c) Darbarwar, M.; Sundaramurthy, V. Synthesis of coumarines with 3:4-fused ring systems and their physiological activity. Synthesis 1982, 337-388, and references therein;
18. (d) O'Callaghan, C. N. Synthesis of dialkyl 2-(2-hydroxyphenyl)-4,6- dimethyl-1,2-dihydropyridine-3,5-dicrboxylates and alkyl 2,4-dimethyl-5-oxo-5H- [1]benzopyrano[4,3-b]pyridine-3-carboxylates. Synthesis 1987, 499-503;
19. (e) Heber, D.; Ivanov, I. C.; Karagiosov, S. K. The Vilsmeier reaction in the synthesis of 3-substituted [1]benzopyrano[4,3-b]pyridine-5-ones. J. Het. Chem. 1995, 505-509;
20. (f) Ghosh, C. K.; Ray, A.; Patra, A. Benzopyrans, part 42[1]: Reactions of 4-oxo-4H-1-benzopyran-3-carbaldehyde with some active methylene compounds in the presence of ammonia. J. Het. Chem. 2001, 1459-1463;
21. (g) Murphy, P. J.; Brennan, J. The Wittig olefination reaction with carbonyl compounds other than aldehydes and ketones. Chem. Soc. Rew. 1988, 17, 1-30;
22. (h) Pars, H. G.; Granchelli, F. E.; Razdan, R. K.; Keller, J. K. Drugs derived from cannabinoids, 1: Nitrogen analogs, benzopyranopyridines and benzopyranopyrroles. J. Med Chem. 1976, 19, 445-454;
23. (i) Pars, H. G.; Granchelli, F. E.; Keller, J. K.; Razdan, R. K. Physiologically active nitrogen analogs of tetrahydrocannabinols: Tetrahydrobenzopyrano[3,4-d]pyridines. J. Am. Chem. Soc. 1966, 88, 3664-3665;
24. ( j) Palacios, F.; Alonso, C.; Amezua, P.; Rubiales, G. Synthesis of aza polycyclic compounds derived from pyrrolidine, indolizidine and indole via intramolecular Diels-Alder cycloadditions of neutral 2-azadienes. J. Org. Chem. 2002, 67, 1941-1946;
25. (k) Pandya, S. U.; Pandya, U. R.; Hirani, B. R.; Brahmbhatt, D. I. One pot synthesis of diarylpyrido[3,2-c]coumarins. J. Heterocycl. Chem. 2006, 43, 795-798.
26. (a) Becalli, E. M.; Contini, A. C.; Trimarco, P. New synthetic approach to [1]benzopyrano[4,3-b]pyridin-5-one derivatives. Tetrahedron Lett. 2004, 45, 3447-3449;
27. (b) Becalli, E. M.; Contini, A. C.; Trimarco, P. Substituted coumarin amidines: Useful building blocks for the preparation of [1]benzopyrano[4,3-b] pyridine-5-one and [1]benzopyrano[4,3-d]pyrimidine-5-one derivatives. Tetrahedron 2005, 61, 4957-4964.
28. (a) Ivanov, I. C.; Karagiozov, S. K.; Manolov, I. Synthesis of 4-(monoalkylamino)-coumarins. Arch. Pharm. 1991, 324, 61-62;
29. (b) Ivanov, I. C.; Karagiozov, S. K.; Simeonov, M. F. A facile synthesis of [1]benzopyrano[4,3-b]pyridine-5-ones. Liebigs Ann. Chem. 1992, 203-207. For additional information on Vilsmeier-Haak formylation of 4-aminocoumarins, see also Ref. 2d.
30. Ivanov, I. C.; Glasnov, T. N.; Heber, D. Synthesis of 2H-chromeno[4,3-b]pyridine-2,5(1H)-diones and related heterocycles via the Erlenmeyer-Ploechl reaction. J. Heterocycl. Chem. 2005, 42, 857-861.
31. (a) Rad-Moghadam, K.; Mohseni, M. A route to the synthesis of novel coumarins. Monats. Chem. 2004, 135, 817-821;
32. (b) Adib, M.; Sayahi, M. H. An efficient onepot synthesis of 4H-pyrrolo[3,2,1-ij]quinolines. Monatsh. Chem. 2006, 137, 207-211;
33. (c) Yavari, I.; Adib, M.; Hojabri, L. Vinyltriphenylphosphonium salt mediated synthesis of functionalized coumarines. Tetrahedron 2001, 57, 7537-7540;
34. (d) Heys, L.; Murphy, P. J.; Coles, S. J.; Gelbirch, T.; Hursthouse, M. B. Intramolecular Wittig reactions with lactones utilizing triphenylphosphine and dimethyl acetylenedicarboxylate. Tetrahedron 1999, 40, 7151-7152;
35. (e) Azizian, J.; Karimi, A. R.; Arefrad, H.; Mohammadi, A. A.; Mohammadizadeh, M. R. Synthesis of some novel γ-spirolactones. Monatsch. Chem. 2004, 135, 729-733;
36. (f) Yavari, I.; Samzadeh-Kermani, A. R. Vinylphosphonium salt mediated steroselective synthesis of cyclobutene derivatives. A facile route to highly electron-deficient 1,3-dienes 1998, 39, 6343-6344;
37. (g) Evans, L. A.; Griffiths, K. E.; Guthmann, H.; Muphy, P. J. Intramolecular Wittig reactions with esters utilizing triphenylphosphine and dimethyl acetylene-dicarboxylate. Tetrahedron Lett. 2002, 43, 299-301.