Synthesis Of 2-(1H-pyrrole-carboxamido) Acetate And Its Derivatives

This thesis has expounded the synthesis of methyl 2-(lH-pyrrole-carboxamido) acetate and its derivatives. Starting from the pyrrole, experiencing several reactions and optimizing the technique conditions, we obtained target compounds. It is found that some compounds have certain activity in anti-bacteria and anti-tumor. There are four parts in this thesis.In chapter one, an overall review is presented at the beginning on the development of separation, activity and synthesis of Aldisin and its related pyrrole alkaloid. On the basis of referring the literature, we designed the way of total synthesis of methyl 2-(1H-pyrrole-carboxamido) acetate and its derivates, using inexpensive and facile materials, and summarizing the result of this research.We expounded the N-alkylation, tricholroacetylation and bromination of pyrrole in chapter two. First, in the presence of TBAB, KOH and alkyl halogen, three N-alkylpyrrole were synthesized. Secondly, 2-trichloroacetylpyrrole were synthesized in the diethyl ether anhydrous at room temperature. Finally, with controlling the reactants' molar ratio, four bromo-derivatives were synthesized from 2-trichloroacetylpyrrole and bromine in the carbon tetrachloride at room temperature.In chapter three, we expounded the synthesis of methyl 2-(1H-pyrrole-carboxamido) acetate. Eighteen series target compounds were synthesized via acylamiction of 2-trichloroacetylpyrrole and methyl 2-aminoaectate hydrochloride in the presence of riethylamine at room temperature. It is found that some compounds have some activity in anti-bacteria and anti-tumor.In the last chapter, it is found that 2-(1H-pyrrole-2-carboxamido) acetate was transformed to sodium 2-(1H-pyrrole-2-carboxamido) acetate in the NaOH-EtOH solvent, and obtained corresponded 2-(1H-pyrrole-2-carboxamido) acetic acid via acidification of the latter. In the presence of PPA and P2O5, 2-(4-bromo-l -methyl- 1H-pyrrole-2-carboxamido) acetic acid was cycled to 3-bromo5,6-dihydro-1 -methyl-1H-pyrrolo[2,3-c]pyridine-4,7-dione.Mostly, there is no literature reference compared to upwards synthesized compounds. We purified every compounds via recrystal and chromatogram, confirmed the structure by EA, NMR, IR, MS and other properties. Some were characterized by single-crystal X-ray diffraction analysis. The reaction conditions, reaction mechanism and spectrum data have been deeply described and discussed.