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Three-component synthesis of 2-haloalk-2(Z)-en-1-ols via tandem haloalkylidenation–aldehyde addition

✍ Scribed by Rachid Baati; D.K. Barma; J.R. Falck; Charles Mioskowski

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
67 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cr(II)-induced condensation of CCl 4 or CBr 4 with an aldehyde stereospecifically generates an (E)-a-haloalkylidene chromium carbenoid which adds in situ to a second equivalent of aldehyde furnishing 2-haloalk-2(Z)-en-1-ols in high yield.

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CrCl 2 converts trichloromethylcarbinols under mild conditions to (E)-a-haloalkylidene chromium carbenoids which add to aldehydes or are quenched with water affording 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes, respectively, in high yield.

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Synthesis of imidazo[1,2a]pyridines via
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A novel three-component reaction towards the synthesis of imidazo [1,2a]pyridines was independently developed based on 2-aminopyridines, aldehydes and alkynes, and thereby imidazo[1,2a]pyridines were obtained in acceptable yields by the CuSO4/TsOH catalyzed three-component reaction.