New and Facile Synthesis of Substituted Pyrrole, Pyridine, Pyrazolo[4,3-b] Pyridine, Pyrano[3,2-c] Quinoline, Napthopyran, Naphthodipyran and Coumarin Derivatives

Abstract

Several new pyrazolo[4,3-b] pyridines 7a, b were prepared by reacting arylidenemalononitriles 1a, c or 1i, j with 4-nitrosoantipyrine 4. Reacting 1a, b, d with 4-azidomethylcarbonylantipyrine 8 give 2-aminopyrrole 14. Pyrano[3,2-c] quinolines 20a, b and 23 were obtained by reacting 4-hydroxyquinoline 15 with 1g, h, 2b respectively. Reaction of 1 with naphthalenediols 24, 27 and 29 yield naphthodipyrans 26a, b, 28a, b and 30a,<

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F. El-Taweel and A. Elagamey, "New and Facile Synthesis of Substituted Pyrrole, Pyridine, Pyrazolo[4,3-b] Pyridine, Pyrano[3,2-c] Quinoline, Napthopyran, Naphthodipyran and Coumarin Derivatives," International Journal of Organic Chemistry, Vol. 3 No. 1, 2013, pp. 58-70. doi: 10.4236/ijoc.2013.31007.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] E. Abd El-Rady and I. H. El-Azab, “Reactivity of β-Enaminoester of Benzo[f] Chromene: One Pot Synthesis of Isolated Heterocycle-Fused Derivatives of Benzo[f] Chromene,” European Journal of Chemistry, Vol. 3, No. 1, 2012, pp. 81-86.
[2] H. M. Mohamed, A. H. F. Abd El-Wahab, K. A. Ahmed, A. M. El-Agrody, A. H. Bedair, F. A. Eid and M. M. Khafagy, “Synthesis, Reactions and Antimicrobial Activities of 8-Ethoxycoumarin,” Molecules, Vol. 17, No. 1, 2012, pp. 971-988. doi:10.3390/molecules17010971
[3] B. F. Abdel-Wahab, R. E. Khidre, A. A. Farahat and A. S. El-Ahl, “2-Chloroquinoline-3-aldehyde: Synthesis, Reactions and Applications,” Arkivoc, Vol. 1, 2012, pp. 211- 276.
[4] F. M. A. El-Taweel, “Novel and Facile Synthesis of Thiophene,2H-pyran-2-one, Benzimidazo[1,2-a]pyridine and Pyridine Derivatives,” Phosphorus, Sulfur and Silicon , Vol. 179, No. 1, 2011, pp. 1276-1277. doi:10.1080/10426500490468083
[5] M. M. Ghorab and M. S. Al-Said, “Synthesis and Antitumor Activity of Some Novel Hydrazide,1,2-dihydropyridine, Chromene and Benzochromene Derivatives,” Journal of Heterocyclic Chemistry, Vol. 49, 2012, pp. 272-280.
[6] J. Tois, M. Vahermo and A. Koskinen, “Novel and Convenient Synthesis of 4(1H)quinolones,” Tetrahedron Letter, Vol. 46, No. 5, 2005, pp. 735-737.
[7] M. M. Abdelkhalik, A. M. Eltoukhy, S. M. Agamey and M. H. Elnagdi, “Enaminones as Building Blocks in Heterocyclic Synthesis of Nicotinic Acid: New Synthesis of Nicotinic Acid and Thienopyridine Derivatives,” Journal of Heterocyclic Chemistry, Vol. 41, No. 3, 2004, pp. 431-435. doi:10:1002/ihet.5570410321
[8] E. S. Othman, “Some Nucleophilic Cyclization Reactions with 3-[4-Benzo [1,3]dioxolylmethylene) pyrazolyl]quinoline,” Acta Chimica Slovonica, Vol. 50, 2003, pp. 15-28.
[9] F. M. A. El-Taweel, “Studies with Quinolines: New Syhthetic Routes to 4H,5H,6H,9H-Benzo[ij]pyrano[2,3-b] quinolizine-8-one,4H-pyrano[2,3-b]2H-pyran-2-one and Pyranopyridoquinoline Derivatives,” Journal of Heterocyclic Chemistry, Vol. 42, No. 5, 2005, pp. 943-946. doi:10.1002/jhet.5570420529
[10] A. A. Elagamey, A. A. El-Taweel and R. A. N. Abu El-Enein, “New Synthetic Routes to 1,3,4-Thiadiazole Derivatives,” Phosphorus, Sulfur and Silicon, Vol. 181, 2006, Article ID: 21552176.

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