Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

Abstract

Using K 2 CO 3 as a base and CH 3 CN as solvent, different kinds of N-[5-alkoxy-2(5H)-furanonyl] amino acids were reacted with propargyl bromide via substitution reaction at 40°C to give 16 N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters with the yields of 44-85% (mostly over 74%). The structures of all newly synthesized compounds were elucidated and confirmed by FTIR, UV, 1 H NMR, 13 C NMR, MS, and elemental analysis. The rapid, efficient, and brief synthesis of the series propargyl esters with multiple bioactive units, will afford not only a basis for the activity test of potential drug molecules, but also an important synthetic strategy for 2(5H)-furanone derivatives with polyfunctional groups.

Synthesis and Characterization of Fluorescent Brightening Agents with Chiral 2(5H)-Furanone and Bis-1,2,3-triazole Structure

“…In contrast, the characteristic peak of terminal alkyne proton in N-[5-(S)-menthoxy-2(5H)-furanonyl] amino acid propargyl esters (5) is not observed in the region of 2.54−2.58 ppm. 27 This also proves that the Click reaction of 5 with DASS is successful indeed. In a word, the structures of all newly synthesized compounds (6) are correct, as expected.…”

“…Furthermore, there is a singlet peak in 8.92 ppm from the proton of bis-1,2,3-triazole ring. In contrast, the characteristic peak of terminal alkyne proton in N -[5-( S )-menthoxy-2(5 H )-furanonyl] amino acid propargyl esters ( 5 ) is not observed in the region of 2.54–2.58 ppm . This also proves that the Click reaction of 5 with DASS is successful indeed.…”

“…Starting from furfural (1), and using natural L-menthol, L-amino acid, and propargyl bromide as materials step by step, the intermediate N-[5-(S)-menthoxy-2(5H)-furanonyl] amino acid propargyl esters 5a and 5b (Scheme 1) were prepared according to the literature. 27 2.2. Synthesis.…”

“…Among them, 4,4′-diazidostilbene-2,2′-disulfonate sodium salt tetrahydrate (DASS) was purchased from TCI (Tokyo Chemical Industry Co., Ltd.). Starting from furfural ( 1 ), and using natural l -menthol, l -amino acid, and propargyl bromide as materials step by step, the intermediate N -[5-( S )-menthoxy-2(5 H )-furanonyl] amino acid propargyl esters 5a and 5b (Scheme ) were prepared according to the literature …”

“…However, the studies on the synthesis of chiral 2(5 H )-furanone derivatives with bis-1,2,3-triazole moiety and fluorescent whitening property have never been reported previously. Herein, based on our previous research, ,, we take advantage of the Click reaction ,,− to build bis-1,2,3-triazole moiety, with the intent to combine stilbene sulfonate with 2(5 H )-furanone moiety (see Scheme ). For the first time, the novel FBA ( 6 ) forms simultaneously possessing chiral 2(5 H )-furanone and bis-1,2,3-triazole moieties are synthesized, and their structures and properties are characterized by infrared (IR) spectroscopy, 1 H nuclear magnetic resonance ( 1 H NMR), 13 C NMR, mass spectroscopy (MS), elemental analysis, ultraviolet (UV) analysis, scanning electron microscopy (SEM), and UV protection factor (UPF) testing.…”