Enaminones in heterocyclic synthesis: A novel route to tetrahydropyrimidines, dihydropyridines, triacylbenzenes and naphthofurans under microwave irradiation

Molecules

Volumn 15, Issue 1, 2010, Pages 58-67

  Al Mousawi, Saleh Mohammed ^a   El Apasery, Morsy Ahmed ^a   Elnagdi, Mohamed H ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

Author keywords

Biginelli's condensation; Enaminones; Microwave irradiation with simultaneous cooling; Naphthofuran; Zeolites

Indexed keywords

BENZENE; DIHYDROPYRIDINE DERIVATIVE; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; PYRIMIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

BENZENE; DIHYDROPYRIDINES; FURANS; HETEROCYCLIC COMPOUNDS, 2-RING; MICROWAVES; PYRIMIDINES;

EID: 75749153280     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15010058     Document Type: Article

References (15)

1. Riyadh, S.M.; Abdelhamid, I.A.; Al-Matar, H.M.; Hilmy, N.H.; Elnagdi, M.H. Enamines as precursors to polyfunctional heteroaromatic compounds; a decade of development. Heterocycles 2008, 75, 1849-1905.
2. Stanovnik, B.; Svete, synthesis of heterocycles from alkyl 3-(dimethylamino) propenoates and related enaminones. Chem. Rev. 2004, 104, 2433-2480.
3. Zhu, S.; Zhao, K.; Su, X.; Ji, S. Microwave-assisted synthesis of new spiro[indoline-3,4′-quinoline] derivatives via a one-pot multicomponent reaction. Synth. Commun. 2009, 39, 1355-1366.
4. Loghmani-Khouzani, H. Sabzyan, H, Rezaei-Pooranari, A. Synthesis and structure of α-azo-2-ketomethylquinolines. Dye. Pigment. 2008, 76, 447-454.
5. Al-Omran, F.; Abdel Khalik, M.M.; ElKhair, A.A.; Elnagdi, M.H. Studies with functionally substituted heteroaromatics: A novel route for the synthesis of 1-aryl-6-oxopyridazinones, 1arylpyridazine-6-imines and 1-aryl-6-imino-4- pyridazinals. Synthesis 1997, 91-94.
6. Al-Mousawi, S.; Moustafa, M.S.; Elnagdi, M.H. Studies with enamines: Functionally substituted enamines as aldehyde equivalents in Gewald reaction ARKIVOC, 2008, 10, 17-25.
7. Elassar, A.A.; El-Khair, A.A. Recent developments in the chemistry of enaminones. Tetrahedron 2003, 59, 8463-8480.
8. De Koning, C.B.; Michael, J.P.; Riley, D.L. Formal Synthesis of (5R,8R,8aS)-indolizidine 2091 via enaminones incorporating weinreb amides. Heterocycles 2009, 79, 935-953.
9. Svete, J. Utilisation of chiral enaminones and azomethine imines in the synthesis of functionalised pyrazoles. ARKIVOC 2006, 7, 35-56. (Pubitemid 43049358)
10. Al-Mousawi, S.; John, E.; Al-Kandery, N. Studies with enaminones: Synthesis and chemical reactivity of 2-(4-dimethylamino-2-oxobut-3-enyl)- isoindole-l,3-dione and of 4-(4dimethylamino-2-oxobut-3-enyloxy)-2h-phthalazin- 1-one. J. Heterocycl. Chem. 2004, 41, 381-385. (Pubitemid 38850037)
11. 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.
12. 1H Long - range coupling constants in configuration assignment of some trisubstituted alkenes. Magn. Reson. Chem. 1994, 32, 567-568
13. Nikpour, F.; Mogaddam, B.M. An expedient method to the synthesis of n-substituted 1h-isoindole-1,3(2h)-diones. Heterocycles 2008, 75, 2289-2292.
14. Hekmatshoar, R.; Heravi, M.M.; Baghernejad, B.; Asadolah, K. Microwave-assisted N-alkylation of potassium phthalimide and potassium succinimide onto silica gel in dry media. Phos. Sulf Silic. 2004, 179, 1611-1614. (Pubitemid 39164133)
15. Al-Mousawi, S.M.; El-Apasery, M.A.; Al-Kanderi, N.H. Azolylacetones as precursors to indoles and naphthofurans facilitated by microwave irradiation with simultaneous cooling. Molecules 2009, 14, 2976-2984.