First diels - Alder reactions of 3-styrylchromones under microwave irradiation

Synlett

Volumn , Issue 10, 2003, Pages 1415-1418

  Pinto, Diana C G A ^a   Silva, Artur M S ^a   Almeida, Lúcia M P M ^a   Carrillo, José R ^b   Díaz Ortiz, Angel ^b   De La Hoz, António ^b   Cavaleiro, José A S ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

3 styrylchromones; Diels Alder reactions; Microwave irradiation; N methyl; N phenylmaleimide

Indexed keywords

CHROMONE DERIVATIVE; IMIDE; METHYL GROUP; N PHENYLMALEIMIDE; SOLVENT; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; MICROWAVE IRRADIATION;

EID: 0042570653     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40826     Document Type: Article

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26. Typical Experimental Procedure: A mixture of N-methyl-maleimide and the appropriate 3-styrylchromone (1 or 5) (4:1 mole ratio) was irradiated at atmospheric pressure in a focused microwave reactor (Prolabo MX350) at 270 W for 30 min (final temperature 160 °C). The crude products were purified by flash chromatography on silica gel (Merck type 60, 230-400 mesh), using a 2:1 mixture of hexane:ethyl acetate.
27. Typical Experimental Procedure: A mixture of the appropriate 3-styrylchromone (1 or 5) and N-phenylmaleimide (1:3 mole ratio) was irradiated at atmospheric pressure in a focused microwave reactor (Prolabo MX350) at 270 W for 30 min (final temperature 200 °C, except for 4′-ethoxy-2-styrylchromones 1c or 5c which was 160 °C). The crude products were purified by flash chromatography on silica gel (Merck type 60, 230-400 mesh); using a 4:1 mixture of hexane:EtOAc the endo cycloadducts were collected while the exo cycloadducts were eluted with a 2:1 mixture of hexane:EtOAc.
28. +], 307 (50), 281 (60), 268 (43), 247 (7), 215 (14), 197 (27), 188 (25), 152 (45), 136 (11), 121 (64), 92 (20), 77 (11), 63 (14).
29. +], 330 (14), 301 (9), 273 (100), 247 (36), 215 (13), 197 (55), 183 (22), 171 (25), 152 (75), 139 (16), 131 (32), 121 (77), 110 (32), 103 (21), 91 (65), 77 (72), 64 (43).
30. +], 301 (17), 273 (4), 154 (100), 120 (20), 92 (23), 77 (6), 64 (6).