Abstract
We report herein the first synthesis of propargylic alcohols using an organic reducing agent. Diarylbutynol derivatives are formed in moderate to good yields under mild conditions from the reaction of 1-(3-chloroprop-1-ynyl)-4-nitrobenzene with various aromatic aldehydes using tetrakis(dimethylamino)ethylene (TDAE) as reductant.
Highlights
Propargylic alcohol derivatives have a major role to play in medicinal chemistry
In continuation of our research program directed towards the development of original synthetic methods in medicinal chemistry [23,24,25,26,27,28], we examined the use of TDAE methodology in the alkyne series
In order to generalize and to confirm this new and original methodology of synthesizing diarylbutynol derivatives, we extended this study to other aromatic aldehydes using an optimized protocol
Summary
Propargylic alcohol derivatives have a major role to play in medicinal chemistry They can act as intermediates for many complex organic molecules with valuable biological activities [1,2], for example efavirenz (Figure 1), an antiretroviral agent. We explored the concept of Long-Distance-SRN1 (LD-SRN1) on a propargylic chloride derivative such as 1-(3-chloroprop-1-ynyl)-4-nitrobenzene [22]. This latter compound constitutes a potential substrate for the preparation of a propargylic anion using the TDAE strategy. We report the synthesis of diarylbutynol derivatives from the reaction of 1-(3-chloroprop-1-ynyl)-4nitrobenzene with various aromatic aldehydes in the presence of TDAE
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