Novel microwave-assisted [3+3] cyclocondensations with 1-cyanomethylene tetrahydroisoquinoline

Synlett

Volumn , Issue 2, 2003, Pages 250-252

  Nemes, Péter ^a   Vincze, Zoltán ^a   Balázs, Barbara ^b   Tóth, Gábor ^b   Scheiber, Pál ^a  

^a SZENT ISTVÁN UNIVERSITY   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

Benzo a quinolizines; Michael additions; Microwave heating; 3+3 cyclisations; enaminonitriles

Indexed keywords

1 CYANOMETHYLENE TETRAHYDROISOQUINOLINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; POLYMERIZATION;

EID: 0037281861     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36796     Document Type: Article

References (10)

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9. Experimental procedure: 2.4 mmol (520 mg) of 1 was mixed with 3.2 mmol of the carbonyl compound, and the reaction mixture was irradiated in an open vessel for 4 minutes in a Synthewave S402 (Prolabo) monomode, focused MW (2,45 GHz) reactor with continuous rotation. During the irradiation, the temperature of the reaction mixture (measured by infrared thermometry) raised linearly and reached its maximum between 140-170°C depending on the enone after ca. 180 seconds. The oily mixture was then cooled and the product was either crystallised from an appropriate solvent (EtOH) or purified by flash chromatography. Yield: 72-85%.
10. 13C NMR δ = 151.6 (C-1), 151.0 (C-6), 147.2 (C-7), 138.1 (Ph), 131.8 (C-4a), 128.6 (Ph), 123.4 (C-2′), 126.2 (Ph), 125.3 (Ph), 122.0 (1′-CN), 120.6 (C-8a), 123.7 (C-3′), 113.2 (C-8), 110.8 (C-5), 77.2 (C-1′), 56.3 7-MeO), 56.0 (6-MeO), 39.6 (C-3), 30.1 (C-4).