One-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides in aqueous conditions

Synthetic Transformations of Sesquiterpene Lactones. 8*. Synthesis of 13-(2-Oxofuro- [2,3-d]pyrimidin-3(2H)-yl)eudesmanolides

“…The 1 Н NMR spectra of compounds 10, 11, 19, 28-31 contained singlets for the protons of furo-[2,3-d]pyrimidine substituent at 8.18-8.47 (H-4') and 6.18-7.22 ppm (H-5'), that was in agreement with the spectral data for analogous compounds [16,17].…”

“…Similar stereoselectivity was also observed before in aza-Michael reactions of isoalantolactone 1 with various amines and alkaloids [14]. The approach of 5-alkynylpyrimidine cyclization has recently attracted significant interest as an effective method for the preparation of furo [2,3-d]pyrimidin-3(2H)-ones [15][16][17]. Such reactions occur under mild conditions by using salts of silver [18], zinc [19], copper [4], and palladium [17,20].…”

Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

“…Two years later, Agrofoglio et al developed a one-pot Sonogashira protocol to obtain substituted furopyrimidine nucleosides in aqueous conditions [30]. The conditions of the rection were optimized starting from 5-iodo-2'-deoxyuridine (1) and phenylacetylene.…”

Eucalyptol as a Bio-Based Solvent for Buchwald-Hartwig Reaction on O,S,N-Heterocycles

“…Pursuing our objective of the development of new practices in the synthesis of heterocycles containing oxygen, sulfur and nitrogen, [3][4][5][6][7][8] we explored the potentialities of eucalyptol as a solvent in the Buchwald-Hartwig coupling reaction. This work began with a literature review to identify the best conditions for this kind of transformation.…”