Azolyacetones as precursors to indoles and naphthofurans facilitated by microwave irradiation with simultaneous cooling

Molecules

Volumn 14, Issue 8, 2009, Pages 2976-2984

  Al Mousawi, Saleh Mohammed ^a   El Apasery, Morsy Ahmed ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

Author keywords

Aminoindole; Azolylacetone; Microwave irradiation; Naphthofuran

Indexed keywords

ACETOPHENONE DERIVATIVE; BENZOFURAN DERIVATIVE; HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; PHENACYL BROMIDE; PHENYLHYDRAZONE; PHTHALIMIDE; PHTHALIMIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ACETOPHENONES; BENZOFURANS; HYDRAZONES; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MICROWAVES; MOLECULAR STRUCTURE; PHTHALIMIDES;

EID: 69549137902     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14082976     Document Type: Article

References (18)

1. Al-Saleh, B.; Abdelkhalik, M.M.; El-Apasery, M.A.; Elnagdi, M.H. N-azolylmethyl ketones as building blocks in heterocyclic synthesis: Synthesis of new polyfunctionally substituted azolylarylazophenols, azolylpyridones and azolylthiophenes. J. Heterocyclic Chem. 2003, 40, 171-175.
2. Al-Saleh, B.; Behbehani, H.; El-Apasery, M.A.; Einagdi, M.H. Enaminones as building blocks in heterocyclic synthesis. Synthesis of polyfunctionally substituted 3-azolylpyridines and azolylazoloazines by thermal and microwave heating. J. Chem. Res. 2004, 8, 575-577.
3. Al-Mousawi, S.; Abdel-Khalik, M.M.; El-Sherbiny, S.; John, E.; Elnagdi, M.H. Studies with enaminones: reactivity of 1, 5-disubstituted-1, 4-pentadien-3-ones toward electrophilic reagents. A novel route to azolylazines, benzofuranals, pyranones. J. Heterocycl. Chem. 2001, 38, 949-953.
4. Al-Naggar, A.; Abdel-Khalik, M.M.; Elnagdi, M.H. Benzotriazol-1-yl- acetone as a building block in heterocyclic chemistry: A route to benzotriazolylpyridazines, benzotriazolyl-phthalazines and benzotriazolylpyrazolo [5, 1-c]-1, 2, 4-triazines. J. Chem. Res. (s) 1999, 11, 648-649, (M), 2801-2810.
5. Al-Saleh, B.; El-Apasery, M.A. Studies with condensed aminothiophenes: Further investigation on the reactivity of condensed aminothiophenes toward electron poor olefins and acetylenes under microwave heating. J. Heterocycl. Chem. 2006, 43, 559-564.
6. Al-Mousawi, S.; John, E.; Al-Kandery, N. Studies with enaminones: Synthesis and chemical reactivity of 2-(4-dimethylamino-2-oxobut-3-enyl)- isoindole-1, 3-dione and of 4-(4-dimethylamino- 2-oxobut-3-enyloxy)-2H- phthalazin-1-one. J. Heterocycl. Chem. 2004, 41, 381-385.
7. Al-Omran, F.; El-Khair, A.A. Heterocyclic synthesis via enaminones: Novel synthesis of (1H)- pyridin-2-one, pyrazolo[1, 5-a]pyrimidine and isoxazole derivatives incorporating a Nmethylphthalimide and their biological evaluation. J. Heterocycl. Chem. 2005, 42, 307-312.
8. Al-Omran, F.; El-Khair, A.A. 2-(3-Arylhydrazono-3-formyl-2-oxopropyl)-1H- isoindole-1, 3(2H)- dione in heterocyclic synthesis. Novel derivatives of pyridazin-6(1H)-one, pyridazin-6(1H)-imine, and pyrazolo[5, 1-c][1, 2, 4]triazine incorporating an N-(2-oxoethyl)phthalimide moiety. J. Chem. Res. 2006, 1, 6-9.
9. Al-Mousawi, S.M.; El-Apasery, M.A.; Al-Kanderi, N.H. Microwave-assisted organic synthesis: The Gabriel approach as a route to new pyrazolylhydrazonoazoles. ARKIVOC 2008, 16, 268-278.
10. De Paulis, T.; Hemstapat, K.; Chen, Y.; Zhang, Y.; Saleh, S.; Alagille, D.; Baldwin, R.M.; Tamagnan, G.D.; Conn, P.J. Substituent effects of N-(1, 3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes. J. Med. Chem. 2006, 49, 3332-3344.
11. Sun, J.; Yan, C. Catalytic synthesis of N-alkylphthalimides under microwave irradiation. Huaxue Yanjiu 2002, 13, 39-40; [Chem. Abstr. 138: 187594].
12. Goossen, L.J.; Ghosh, K. Palladium-catalyzed synthesis of aryl ketones from boronic acids and carboxylic acids activated in situ by pivalic anhydride. Eur. J. Org. Chem. 2002, 19, 3254-3267.
13. Katritzky, A.R.; Wrobel, L.; Savage, G.P.; Deyrup-Drewniak, M. The formation of ketones by a reaction equivalent to R- + R'COCH2+ R'COCH2R. Aust. J. Chem. 1990, 43, 133-139.
14. Katritzky, A.R.; Wu, J.; Wrobel, L.; Rachwal, S.; Steel, P.J. Novel conversions of benzotriazol-1- ylmethyl derivatives. Acta Chem. Scand. 1993, 47, 167-175.
15. Anderson, D.J.; Gilchrist, T.L.; Gymer, G.E.; Rees, C.W. Reactive intermediates. XXII. Formation of 2H-azirines by oxidation of N-aminophthalimide in the presence of alkynes. J. Chem. Soc. Perk. Trans.1 1973, 6, 550-555.
16. Bahekar, R.H.; Jain, M.R.; Goel, A.; Patel, D.N.; Prajapati, V.M.; Gupta, A.A.; Jadav, P.A.; Patel, P.R. Design, synthesis, and biological evaluation of substituted-N-(thieno[2, 3-b]pyridin-3-yl)- guanidines, N-(1H-pyrrolo[2, 3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines. Bioorg. Med. Chem. 2007, 15, 3248-3265.
17. Al-Mousawi, S.M.; El-Apasery, M.A.; Elnagdi, M.H. Studies with condensed aminothiophenes: Microwave assisted cycloaddition reactions of thieno[3, 4-d]pyridazinone and thieno[3, 4- c]quinolinone. Heterocycles 2008, 75, 1151-1161.
18. Hassanien, A.A.; Ghozlan, S.A.S.; Elnagdi, M.H. Studies with functionally substituted methylbenzotriazoles: Novel synthesis of functionally substituted pyrazolo[5, 1-c]-1, 2, 4-triazines benzotriazol-1-yl, 1-pyrazol-4-yl benzotriazoles and 1-isoxazol-4-yl benzotriazoles. J. Chin. Chem. Soc. 2004, 51, 575-579.