Pictet-Spengler heterocyclizations via microwave-assisted degradation of DMSO

Tetrahedron Letters

Volumn 46, Issue 14, 2005, Pages 2465-2468

  Mésangeau, Christophe ^a   Yous, Saïd ^a   Pérès, Basile ^a   Lesieur, Daniel ^a   Besson, Thierry ^b  

^a UNIV LILLE   (France)

^b UNIVERSITÉ DE LA ROCHELLE   (France)

Author keywords

Dimethyl sulfoxide; Formaldehyde; Microwave assisted reactions; Pictet Spengler heterocyclization

Indexed keywords

DIMETHYL SULFOXIDE; MELATONIN;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; DECOMPOSITION; DEGRADATION; MICROWAVE RADIATION; PICTET SPENGLER REACTION; SYNTHESIS;

EID: 17744371332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.043     Document Type: Article

References (28)

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23. TM). The instrument consists of a continuous focused microwave power output from 0 W to 300 W. Reactions were performed in a glass vessel prolonged by a condenser; it is also possible to work under dry atmosphere, in vacuo, or under pressure (0-20 bar, tubes of 10 mL, sealed with a septum) if necessary (warning: the use of decomposing solvent in sealed vessel may be dangerous even with pressure and temperature control). The temperature content of a vessel is monitored using calibrated infrared sensor mounted under the vessel. All the experiments were performed using stirring option whereby the contents of a vessel are stirred by means of a rotating plate located below the floor of the microwave cavity and a Teflon-coated magnetic stir bar in the vessel. In all experiments a target temperature of 190°C (DMSO bp: 189°C) was selected together with a power of 140 W. The target temperature was reached with a ramp of 2 min and the microwave power stay constant to hold the mixture at this temperature. The time of the reaction does not include the ramp period
24. 4) and evaporated under reduced pressure. Recrystallization from toluene-cyclohexane afforded the expected product
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