The synthesis of 2-substituted indoles starting from the corresponding unprotected 2-alkynylanilines was made possible in 3% TPGS-750-M water using Pd(OAc)2 alone as the catalyst. The reaction was sensitive to the heating mode respect to the nature of the starting material as, in many cases, convectional heating was better than microwave dielectric heating. The MW (microwave) delivery mode had also an influence in the formation of by-products and, consequently, product yields. A tandem Sonogashira-cyclisation reaction was also accomplished using Pd(OAc)2/Xphos in the nanomicellar water environment.
Dedicated to Professor Cesare Gennari on the occasion of his 70th birthdayEthyl diazoacetate (EDA), which is easily prepared from ethyl glycinate and NaNO 2 , reacts in situ with alkynes in a water micelle environment without organic solvent to form pyrazoles. The reaction is pH dependent, as in the presence of protic catalysis (H 2 SO 4 4 %, pH 3.5) a mixture of 3,5-and 4,5disubstituted pyrazoles was obtained, while, at pH 5.5, only the 3,5-disubstituted isomer was obtained. The presence of the surfactant TPGS-750-M was crucial to secure clean crude reaction mixtures and high yields of the products. The same protocol was successfully applied to the synthesis of substituted pyrazolines.
Derivatives of 7-hydroxy-5-oxopyrazole[4,3-b]pyridine-6-carboxamide scaffold have been reported recently as potent and selective agonists/inverse agonists of the cannabinoid type-2 receptor (CB2R), but the synthetic way adopted has not yet allowed to...
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