| Pyrrolypyridines as an important class of nitrogen-containing heterocyclic com-pounds are applied to a vast array of materials chemistry including semi-conducting materials, conducting materials and photoelectric material. In additon, many of them are valuable model used to study hydrogen bonding from binding in DNA base pairs to protein folding and enzyme-substrate interactions. Because of their special struc-ture and important application, a rational synthetic strategy towards pyrrolylpyridines was established.In this thesis, N-tosylpyrrole was synthesized in high yield starting from commercially available pyrrole, which then underwent acylation, ring-opening, ring-closing and nucleophilic reaction treatment with POBr3 (or POCl3) to give 2-bromo(or chloro)-6-(1-tosyl-lH-pyrrol-2-yl)pyridine. A series of 2-aryl-6-(1-tosyl-1H-pyrrol-2'-yl)pyridine and 2-aryl-6-(1H-pyrrol-2'-yl)pyridine were obtained in good yields by typical Suzuki cross-coupling reaction of 2-bromo (or chloro)-6-(N-tosylpyrrol-2'-yl)pyridine with arylboronic acids. All the new structures were confirmed on the basis of IR, 1HNMR,13CNMR and MS.In addition, the influences of protecting groups on the ring of 3,4-dihydro-pyridin-2(1H)-one and that on the ring of pyrrole, and 2-halo(Cl and Br) on the ring of pyridine were verified respectively. |
