How to cite this paper
Khalafy, J., Rimaz, M & Ezzati, M. (2012). Regioselective one-pot, three component synthesis of ethyl 6-aryl-3-propylpyridazine-4-carboxylates in water.Current Chemistry Letters, 1(3), 115-122.
Refrences
1. Zhu J. (2003) Recent developments in the isonitrile-based multicomponent synthesis of heterocycles. Eur. J. Org. Chem., 68, 1133-1144.
2. Bienayme H., Hulme C., Oddon G., and Schmitt P. (2000) Maximizing synthetic efficiency: Multi-component transformations lead the way. Chem. Eur. J., 6, 3321-3329.
3. Domling A., and Ugi I. (2000) Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed., 39, 3168-3210.
4. Weber L., Illgen K., and Almstetter M. (1999) Discovery of new multi component reactions with combinatorial methods. Synlett, 366- 374.
5. Dax S. L., McNally J. J., and Youngman M. A. (1999) Multi-component methodologies in solidphase organic synthesis, Curr. Med. Chem, 6, 255-270.
6. Armstrong R. W., Combs A. P., Tempest P. A., Brown S. D., and Keating T. A. (1996) Multiple-component condensation strategies for combinatorial library synthesis, Acc. Chem. Res., 29, 123-131.
7. Orita A., Yoshioka N., Struwe P., Braiser A., Beckmann A., and Otera J. (1999) Integrated chemical process: one-pot double elimination method for acetylenes. Chem. Eur. J., 5, 1355-1363.
8. Grigg R., Liu A., Shaw D., Sunganthan S., Washington M.,Woodall D., and Yoganathan G. (2000) Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels-Alder reactions. Tetrahedron Lett., 41, 7129-7133.
9. Braun R., Zeitter K., and Müller T. (2001) A novel one-pot pyrrole synthesis via a coupling-isomerization-stetter-paal-knorr sequence, Org. Lett., 3, 3297-3300.
10. Clique B., Vassiliou S., Monteiro N., and Balme G. (2002) Integrated transition metal catalyzed reactions: synthesis of polysubstituted 4-(phenoxymethyl)-3-pyrrolines and their isomers by one-pot coupling of propargylamines, vinyl sulfones (or nitroalkenes) and phenols, Eur. J. Org. Chem., 1493-1499.
11. Tamayo N., Liao L., Goldberg M., Powers D., Tudor Y. Y., Yu V., Wong L. M., Henkle B., Middleton S., Syed R., Harvey T., Jang G., Hungate R., and Dominguez, C. (2005) Design and synthesis of potent pyridazine inhibitors of p38 MAP kinase. Bioorg. Med. Chem. Lett., 15, 2409-2413.
12. Nagawade R. R., Khanna V. V., Bhagwat S. S., and Shinde D. B. (2005) Synthesis of new series of 1-Aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents. Eur. J. Med. Chem., 40, 1325-1330.
13. Sotelo E., and Ravina E. (2002) Pyridazine derivatives. XXIV. [1] efficient n-methylation of diversely substituted 3(2H)-pyridazinones using N,N-dimethylformamide dimethylacetal, Synth. Commun, 32, 1675-1680.
14. Coelho A. Sotelo E. Novoa H. Peeters O. M. Blaton N. and Ravina E. (2004) Pyridazine derivatives. Part 38: Efficient Heck alkenylation at position 5 of the 6-phenyl-3(2H)-pyridazinone system, Tetrahedron, 45, 3459-3463.
15. Rohet F. Rubat C. Coudert P., and Couquelet J. (1997) Synthesis and analgesic effects of 3-substituted 4,6-diarylpyridazine derivatives of the arylpiperazine class. Bioorg. Med. Chem., 5, 655-659.
16. Tucker J. A. Allwine D. A. Grega K. C. Barbachyn M. R. Klock J. L. Adamski J. L. Brickner S. J. Hutchinson D. K. Ford C. W. Zurenko G. E. Conradi R. A. Burton P. S. and Jensen R. M. (1998) Piperazinyl oxazolidinone antibacterial agents containing a pyridine, diazene, or triazene heteroaromatic ring, J. Med. Chem, 41, 3727-3735.
17. Benson, S. C., Palabrica C. A., and Snyder J. K. (1987) Indole as a dienophile in inverse electron demand Diels-Alder reactions. 5H-Pyridazino[4,5-b]indoles as cycloadducts with 3,6-dicarbomethoxy-1,2,4,5-tetrazine, J. Org. Chem., 52, 4610-4614.
18. Gyoten M., Nagaya H., Fukuda S., Ashida Y., and Kawano Y. (2003) Synthesis of eosinophil in?ltration inhibitors with antihistaminic activity, Chem. Pharm. Bull., 51, 122-133.
19. Sung N. D., Yung K. S., Kim T. Y., Choi K. Y., Such M., Kim J. G., Suh I. H., and Chin, J. (2001) Synthesis and characterization of a novel tetranuclear nickel(II) complex: [Ni4(?-OH)2(?-dppn)4(?-H2O)2](Cl)(ClO4)5 9H2O (dppn=3,6-bis(2 & apos; -pyridyl)pyridazine). Inorg. Chem. Commun., 4, 377-380.
20. Brooker S., Davidson T. C., Hay S. J., Kelly R. J., Kennepohl D. K., Plieger P. G., Moubaraki B., Murray K. S., Bill E., and Bothe E. (2001) Doubly pyridazine-bridged macrocyclic complexes of copper in + 1, + 2 and mixed valent oxidation states, Coord. Chem. Rev., 216-217, 3-30.
21. Cheng Y., Ma B. and Wudl F. (1999) Synthesis and optical properties of a series of pyrrolopyridazine derivatives: deep blue organic luminophors for electroluminescent devices, J. Mater. Chem., 9, 2183-2188.
22. Rimaz M., and Khalafy J. (2010) Novel one-pot, three component synthesis of alkyl 6-aryl-3-methylpyridazine-4-carboxylates in water. Arkivoc, ii, 110-117.
23. Rimaz M., Khalafy J., and Najafi Moghadam, P. (2010) A regioselective one-pot, three component synthesis of 6-aryl-4-cyano-3(2H)-pyridazinones in water. Aust. J. Chem, 63, 1396-1401.
24. Rimaz M., Khalafy J., Noroozi Pesyan N., and Prager R. H. (2010) A simple one-pot, three component synthesis of 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their sulfur analogues as potential monoamine oxidase inhibitors. Aust. J. Chem., 63, 507-510.
25. Rimaz M., Noroozi Pesyan N., and Khalafy J. (2010) Tautomerism and isotopic multiplets in the 13C NMR spectra of partially deuterated 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their sulfur analogs-evidence for elucidation of the structure backbone and tautomeric forms, Magn. Reson. Chem. 48, 276-285.
26. Khalafy J., Rimaz M., Panahi L., and Rabiei H. (2011). A regiospecific one-pot, three component synthesis of 4-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones as new potential monoamine oxidase inhibitors, Bull. Korean Chem. Soc., 32, 2428-2432.
27. Riley H. A., and Gray A. R. (1943) Phenylglyoxal. Organic Syntheses, Wiley & Sons: New York, NY, Collect. Vol. II, p 509.
2. Bienayme H., Hulme C., Oddon G., and Schmitt P. (2000) Maximizing synthetic efficiency: Multi-component transformations lead the way. Chem. Eur. J., 6, 3321-3329.
3. Domling A., and Ugi I. (2000) Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed., 39, 3168-3210.
4. Weber L., Illgen K., and Almstetter M. (1999) Discovery of new multi component reactions with combinatorial methods. Synlett, 366- 374.
5. Dax S. L., McNally J. J., and Youngman M. A. (1999) Multi-component methodologies in solidphase organic synthesis, Curr. Med. Chem, 6, 255-270.
6. Armstrong R. W., Combs A. P., Tempest P. A., Brown S. D., and Keating T. A. (1996) Multiple-component condensation strategies for combinatorial library synthesis, Acc. Chem. Res., 29, 123-131.
7. Orita A., Yoshioka N., Struwe P., Braiser A., Beckmann A., and Otera J. (1999) Integrated chemical process: one-pot double elimination method for acetylenes. Chem. Eur. J., 5, 1355-1363.
8. Grigg R., Liu A., Shaw D., Sunganthan S., Washington M.,Woodall D., and Yoganathan G. (2000) Palladium-catalysed cascade molecular queuing-cycloaddition, cyclocondensation and Diels-Alder reactions. Tetrahedron Lett., 41, 7129-7133.
9. Braun R., Zeitter K., and Müller T. (2001) A novel one-pot pyrrole synthesis via a coupling-isomerization-stetter-paal-knorr sequence, Org. Lett., 3, 3297-3300.
10. Clique B., Vassiliou S., Monteiro N., and Balme G. (2002) Integrated transition metal catalyzed reactions: synthesis of polysubstituted 4-(phenoxymethyl)-3-pyrrolines and their isomers by one-pot coupling of propargylamines, vinyl sulfones (or nitroalkenes) and phenols, Eur. J. Org. Chem., 1493-1499.
11. Tamayo N., Liao L., Goldberg M., Powers D., Tudor Y. Y., Yu V., Wong L. M., Henkle B., Middleton S., Syed R., Harvey T., Jang G., Hungate R., and Dominguez, C. (2005) Design and synthesis of potent pyridazine inhibitors of p38 MAP kinase. Bioorg. Med. Chem. Lett., 15, 2409-2413.
12. Nagawade R. R., Khanna V. V., Bhagwat S. S., and Shinde D. B. (2005) Synthesis of new series of 1-Aryl-1,4-dihydro-4-oxo-6-methyl pyridazine-3-carboxylic acid as potential antibacterial agents. Eur. J. Med. Chem., 40, 1325-1330.
13. Sotelo E., and Ravina E. (2002) Pyridazine derivatives. XXIV. [1] efficient n-methylation of diversely substituted 3(2H)-pyridazinones using N,N-dimethylformamide dimethylacetal, Synth. Commun, 32, 1675-1680.
14. Coelho A. Sotelo E. Novoa H. Peeters O. M. Blaton N. and Ravina E. (2004) Pyridazine derivatives. Part 38: Efficient Heck alkenylation at position 5 of the 6-phenyl-3(2H)-pyridazinone system, Tetrahedron, 45, 3459-3463.
15. Rohet F. Rubat C. Coudert P., and Couquelet J. (1997) Synthesis and analgesic effects of 3-substituted 4,6-diarylpyridazine derivatives of the arylpiperazine class. Bioorg. Med. Chem., 5, 655-659.
16. Tucker J. A. Allwine D. A. Grega K. C. Barbachyn M. R. Klock J. L. Adamski J. L. Brickner S. J. Hutchinson D. K. Ford C. W. Zurenko G. E. Conradi R. A. Burton P. S. and Jensen R. M. (1998) Piperazinyl oxazolidinone antibacterial agents containing a pyridine, diazene, or triazene heteroaromatic ring, J. Med. Chem, 41, 3727-3735.
17. Benson, S. C., Palabrica C. A., and Snyder J. K. (1987) Indole as a dienophile in inverse electron demand Diels-Alder reactions. 5H-Pyridazino[4,5-b]indoles as cycloadducts with 3,6-dicarbomethoxy-1,2,4,5-tetrazine, J. Org. Chem., 52, 4610-4614.
18. Gyoten M., Nagaya H., Fukuda S., Ashida Y., and Kawano Y. (2003) Synthesis of eosinophil in?ltration inhibitors with antihistaminic activity, Chem. Pharm. Bull., 51, 122-133.
19. Sung N. D., Yung K. S., Kim T. Y., Choi K. Y., Such M., Kim J. G., Suh I. H., and Chin, J. (2001) Synthesis and characterization of a novel tetranuclear nickel(II) complex: [Ni4(?-OH)2(?-dppn)4(?-H2O)2](Cl)(ClO4)5 9H2O (dppn=3,6-bis(2 & apos; -pyridyl)pyridazine). Inorg. Chem. Commun., 4, 377-380.
20. Brooker S., Davidson T. C., Hay S. J., Kelly R. J., Kennepohl D. K., Plieger P. G., Moubaraki B., Murray K. S., Bill E., and Bothe E. (2001) Doubly pyridazine-bridged macrocyclic complexes of copper in + 1, + 2 and mixed valent oxidation states, Coord. Chem. Rev., 216-217, 3-30.
21. Cheng Y., Ma B. and Wudl F. (1999) Synthesis and optical properties of a series of pyrrolopyridazine derivatives: deep blue organic luminophors for electroluminescent devices, J. Mater. Chem., 9, 2183-2188.
22. Rimaz M., and Khalafy J. (2010) Novel one-pot, three component synthesis of alkyl 6-aryl-3-methylpyridazine-4-carboxylates in water. Arkivoc, ii, 110-117.
23. Rimaz M., Khalafy J., and Najafi Moghadam, P. (2010) A regioselective one-pot, three component synthesis of 6-aryl-4-cyano-3(2H)-pyridazinones in water. Aust. J. Chem, 63, 1396-1401.
24. Rimaz M., Khalafy J., Noroozi Pesyan N., and Prager R. H. (2010) A simple one-pot, three component synthesis of 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their sulfur analogues as potential monoamine oxidase inhibitors. Aust. J. Chem., 63, 507-510.
25. Rimaz M., Noroozi Pesyan N., and Khalafy J. (2010) Tautomerism and isotopic multiplets in the 13C NMR spectra of partially deuterated 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their sulfur analogs-evidence for elucidation of the structure backbone and tautomeric forms, Magn. Reson. Chem. 48, 276-285.
26. Khalafy J., Rimaz M., Panahi L., and Rabiei H. (2011). A regiospecific one-pot, three component synthesis of 4-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones as new potential monoamine oxidase inhibitors, Bull. Korean Chem. Soc., 32, 2428-2432.
27. Riley H. A., and Gray A. R. (1943) Phenylglyoxal. Organic Syntheses, Wiley & Sons: New York, NY, Collect. Vol. II, p 509.