Acyl Sonogashira Reactions

Ranjan, Priyadarshi (2011) Acyl Sonogashira Reactions. Masters thesis, Indian Institute of Science Education and Research, Kolkata.

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Abstract

In the first part of the thesis palladium nanocatalyst has been attempted to synthesize 1-(1-benzyl-1H-indol-3-yl)-3-(trimethylsilyl)prop-2-yn-1-one through copper free Sonogashira reaction condition using 1H-indole-3-carbonyl chloride and ethynyltrimethylsilane in order to synthesize intermediate for the synthesis of biologically active meridianin. This intermediate once accomplished can be in priciple used in one-pot three component synthesis following the acyl Sonogashira reaction via the coupling-addition-cyclocondensation sequence. In the second part of the thesis palladium nanoparticles fixed on single walled carbon nanotubes has been synthesized which serve as an efficient and reusable solid support for copper free Sonogashira reaction for acyl chlorides with terminal acetylenes. A wide array of ynones are synthesized in high yields under mild reaction condition. This simple protocol of ynone preparation in high yield was further explored in the multicomponent synthesis of 2,4-disubstituted pyrimidines derivative in one-pot fashion. Disubstituted pyrimidines were obtained in good yields applying one-pot three component synthesis following an acyl Sonogashira coupling-addition-cyclocondensation sequence.

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