Department of Chemistry, College of Science, Princess Nourah Bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi Arabia.
Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo 11711, Egypt.
Molecules. 2024 Sep 22;29(18):4496. doi: 10.3390/molecules29184496.
2-Chloropyridine-3-carbonitrile derivative was utilized as a key precursor to build a series of linear and angular annulated pyridines linked to a 6-hydroxy-4,7-dimethoxybenzofuran moiety. Reaction of substrate with various hydrazines afforded pyrazolo[3,4-]pyridines. Treatment of substrate with 1,3-,-binucleophiles including 3-amino-1,2,4-triazole, 5-amino-1-tetrazole, 3-amino-6-methyl-1,2,4-triazin-5(4)-one and 2-aminobenzimidazole produced the novel angular pyrido[3,2-][1,2,4]triazolo[4,3-]pyrimidine, pyrido[3,2-][1,2,4]tetrazolo[1,5-]pyrimidine, pyrido[3',2':5,6] pyrimido[2,1-][1,2,4]triazine and benzo[4,5]imidazo[1,2-]pyrido[3,2-]pyrimidine, respectively. Reaction of substrate with 1,3-,-binucleophiles including cyanoacetamides and 1-benzimidazol-2-ylacetonitrile furnished 1,8-naphthyridines and benzoimidazonaphthyridine. Moreover, reacting substrate with 5-aminopyrazoles gave pyrazolo[3,4-][1,8]naphthyridines. Finally, reaction of compound with 6-aminouracils as cyclic enamines yielded pyrimido[4,5-][1,8]naphthyridines. Some of the synthesized products showed noteworthy antimicrobial efficiency against all types of microbial strains. Structures of the produced compounds were established using analytical and spectroscopic tools.
2-氯吡啶-3-甲腈衍生物被用作构建一系列连接到 6-羟基-4,7-二甲氧基苯并呋喃部分的线性和角环化吡啶的关键前体。底物与各种肼反应得到吡唑并[3,4-]吡啶。用 1,3-双-亲核试剂处理底物 ，包括 3-氨基-1,2,4-三唑、5-氨基-1-四唑、3-氨基-6-甲基-1,2,4-三嗪-5(4)-酮和 2-氨基苯并咪唑，产生了新型角吡啶并[3,2-][1,2,4]三唑并[4,3-]嘧啶、吡啶并[3,2-][1,2,4]四唑并[1,5-]嘧啶、吡啶并[3',2':5,6]嘧啶并[2,1-][1,2,4]三嗪和苯并[4,5]咪唑并[1,2-]吡啶并[3,2-]嘧啶，分别。用 1,3-双-亲核试剂处理底物 ，包括氰基乙酰胺和 1-苯并咪唑-2-乙腈，得到 1,8-萘啶和苯并咪唑并萘啶。此外，将底物与 5-氨基吡唑反应得到吡唑并[3,4-][1,8]萘啶。最后，用环状烯胺 6-氨基尿嘧啶与化合物 反应得到嘧啶并[4,5-][1,8]萘啶。一些合成产物对所有类型的微生物菌株表现出显著的抗菌效率。通过分析和光谱工具确定了所产生化合物的结构。
