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Synthesis 2012; 44(16): 2519-2526
DOI: 10.1055/s-0031-1290809
DOI: 10.1055/s-0031-1290809
special topic
An Efficient Synthesis of 2-(Trifluoromethyl)-2H-[1,3]oxazino[2,3-a]isoquinolines via a Three-Component Cascade Approach Using a Continuous-Flow Microreactor
Further Information
Publication History
Received: 18 February 2012
Accepted: 05 March 2012
Publication Date:
08 May 2012 (online)
Abstract
The three-component reaction between an isoquinoline, a dialkyl acetylenedicarboxylate and 2,2,2-trifluoro-1-phenylethanone involving a 1,4-dipolar cycloaddition cascade approach is developed using a continuous-flow microreactor. The reaction conditions (solvent, flow rate and temperature) are optimized leading to the synthesis 2-(trifluoromethyl)-2H-[1,3]oxazino[2,3-a]isoquinoline derivatives in 79-83% isolated yields, whilst eliminating the formation of 11bH-pyrido[2,1-a]isoquinoline-1,2,3,4-tetracarboxylate by-products. The continuous-flow method is also applied to similar reactions using aromatic aldehydes as the carbonyl component.
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