Furan derivatives. 1С. Role of acetic anhydride in nitration of 3-(2-furyl)acryIic acid
نویسندگان
چکیده
An exothermic reaction, leading to 3-(2-furyl)acrylic anhydride and a little amount of furfurylideneacetone is taking place when reacting 3-(2-furyl)acrylic acid in acetic anhydride above 120°C. The 3-(5-acetyl-2-furyl)acrylic acid was formed under the afore-mentioned conditions only in the presence of H 3 P 0 4 . The 3-(2-furyl)acrylic anhydride is more stable towards HNO, at temperatures under — 5°C than the free acid and therefore, it was possible to nitrate it in acetic anhydride to 3-(5-nitro-2-furyl)acrylic acid with an H N 0 3 — C H 3 C O O H mixture, which means a simplification of the nitration process.
منابع مشابه
Synthesis and electrophilic substitutions of novel pyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidines.
5-Aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines 1 were used as precursors for the preparation of a new series of 5-aryl-8-phenylpyrazolo[1,5-c]-1,2,4- triazolo[4,3-a]pyrimidines 2. The reactions of 2 with certain electrophilic reagents gave the respective 6-substituted derivatives 3-5 rather than the 7-isomeric products. Formylation of the key compounds 1 with ethyl formate yielded the fo...
متن کاملNovel N-2-(Furyl)-2-(chlorobenzyloxyimino) ethyl Piperazinyl Quinolones: Synthesis, Cytotoxic Evaluation and Structure-activity Relationship
Quinolone antibacterials are one of the most important classes of pharmacological agents known as potent inhibitors of bacterial DNA gyrase and topoisomerase IV that efficiently inhibit DNA replication and transcription by generating several double-stranded DNA break. Some quinolone derivatives demonstrated inhibitory potential against eukaryote topoismarase II and substantial dose-dependent cy...
متن کاملNucleic Acid Related Compounds. 107. Efficient Nitration of Uracil Base and Nucleoside Derivatives(1).
The 5′-phosphate ester of 5-nitro-2′-deoxyuridine (7c) is a potent mechanism-based inhibitor of thymidylate synthase.2 Compound 7c3 and 1-(â-D-arabinofuranosyl)5-nitrouracil4 have antiviral activity, and certain O-nitro esters of pyrimidine5 and purine6 nucleosides also have biological activity. The 5′-O-nitro esters of pyrimidine nucleosides function as good substrates for 5′-modification via ...
متن کاملNovel N-2-(Furyl)-2-(chlorobenzyloxyimino) ethyl Piperazinyl Quinolones: Synthesis, Cytotoxic Evaluation and Structure-activity Relationship
Quinolone antibacterials are one of the most important classes of pharmacological agents known as potent inhibitors of bacterial DNA gyrase and topoisomerase IV that efficiently inhibit DNA replication and transcription by generating several double-stranded DNA break. Some quinolone derivatives demonstrated inhibitory potential against eukaryote topoismarase II and substantial dose-dependent cy...
متن کاملScandium(III) trifluoromethanesulfonate catalyzed aromatic nitration with inorganic nitrates and acetic anhydride.
The rare earth metal(III) trifluoromethanesulfonate (rare earth metal(III) triflate, RE(OTf)3) was found to be an efficient catalyst for aromatic nitration with carboxylic anhydride-inorganic nitrate as the nitrating agent. In the presence of a catalytic amount of RE(OTf)3, the nitration of substituted benzenes proceeded to afford the corresponding nitrobenzenes. Especially, scandium(III) trifl...
متن کامل