Synthesis of new derivatives of 2-chloro-3-formyl-1,8-naphthyridine

Abstract

A simple and regioselective synthesis of 2-chloro-3-formyl-1,8-naphthyridine, through Vilsmeier-Haack cyclization of N-(pyridin-2-yl)acetamide has been reported. The reaction of 2-chloro-3-formyl-1,8-naphthyridine is also investigated and new series of 1,8-naphthyridine derivatives such as 3-chloro-4-(2-chloro-1,8-naphthyridine-3-yl)-1-(phenylamino)azetidin-2one, 3-chloro-4-(2-chloro-1,8-naphthyridin-3yl)-1-((4-nitrophenyl) amino)-azetidin-2-one and 3-chloro-4-(2-chloro-1,8-naphthyridine-3-yl)-1-((2,4-dinitrophenyl) amino)-azetidin-2one have been prepared. The formyl group in the 1,8-naphthyridine is subjected to further transformation into alkoxy carbonyl (NIS-K2CO3/alcohol) to afford 3-alkoxy carbonyl-1,8naphthyridine and new hetero cyclic compounds such as oxadiazolo, thiadiazolo-thion and triazolo-thion have been prepared. The reaction between 2-chloro-3-formyl-1,8naphthyridine and sodium sulphide in DMF produced 2-mercapto-3-formyl-1,8naphthyridine. Some of the prepared compounds were found to have good biological activity against Staphylococcus aureus and Staphylococcus epidermidis.Triazol Thiadizol Azetidine Oxadiazol Naphthyridine Vilsmeier-Haack

Synthesis biological studies of some new heterocyclic compound derived from 2-chloro-3-formyl quinoline and 4-(benzyl sulfonyl) acetophenone

“…Chalcones and their derivatives are also medically important. Many chalcones compounds are important class of natural products and as a precursor for synthesis of various heterocyclic compounds like imidazole, pyrazoles, pyrazoline, azetidine, triazole, thiazole and oxadiazole [16][17][18][19] have been reported to posses anti-malaria, anti-inflammatory and antibacterial activity [20,21] . Recently interest in the sulfur-heterocycles compounds have significantly increased since a wide range of biological activities [22] .…”

Synthesis, Biological Evaluation and Molecular Docking Studies of Novel 1,8-Naphthyridine-3-carboxylic Acid Derivatives as Potential Antimicrobial Agents (Part-1)

“…Based on the above information, a novel series of compounds in this class were synthesized with an objective to obtain effective yet non-mutagenic derivatives. The 1,8-naphthyridine nuclei are found in well-known antibacterial compounds [15] called quinolones ( fig. 1), which act as DNA gyrase inhibitors [16] .…”

Practical Synthesis of 1,8-Naphthyridine-2,7-dialdehydes Syntone

“…Synthesis of 1,8-naphthyridine [13] is carried out by using the following reaction (eqn 4) which is followed by replacing of chlorine atom with methyl group (eqn 5), however these reactions did not work either. Synthesis of naphthyridine using eqn 4 is failed in our lab.…”