Synthesis of a New Polyfunctionalised Pyrimidine-4-carboxylate and Its Application for the Construction of a Series of Pyrimidine Derivatives

Abstract

The synthesis of a new and versatile polyfunctionalised pyrimidine-4-carboxylate, along with the study of its reactivity against 1,2-dinucleophiles and 1,4-dinucleophiles, is reported. These simple and efficient methodologies allowed for the synthesis of novel pyrimidine derivatives such as pyrimido[4,5-d]pyridazin-8-one-5-carboxylates and their corresponding carbohydrazides and N-acylhydrazone (NAH) derivatives, pyrimido[4,5-d][1,2]oxazin-8-one and its corresponding carbohydrazide derivative, and 3-pyrimidinylquinoxaline-2-one and its corresponding carbohydrazide. Furthermore, pyrimidine hydroxyimino derivatives were also prepared.

Design, synthesis, and exploration of antibacterial activity of 6H-1,2-oxazin-6-ones

“…These results are consistent with oxazinone yields lower than 70% reported in previous studies and the tendency for yields to be lower when halogen is the substituent. 18,32,57,58 Only Gonçalves et al (2016) and Shamala, D. and Shivashankar, K. (2017) reported yields greater than 90%, achieved using pyridine and DBU as catalysts under basic reaction conditions. 58,59…”

“… 18,32,57,58 Only Gonçalves et al (2016) and Shamala, D. and Shivashankar, K. (2017) reported yields greater than 90%, achieved using pyridine and DBU as catalysts under basic reaction conditions. 58,59 …”

“…18,32,57,58 Only Gonçalves et al (2016) and Shamala, D. and Shivashankar, K. (2017) reported yields greater than 90%, achieved using pyridine and DBU as catalysts under basic reaction conditions. 58,59 The structure of the 12 6H-1,2-oxazin-6-ones was conrmed using FTIR, MS(EI), 1 H, and 13 C NMR analytical techniques (ESI †). X-ray diffraction was employed for those compounds where a block crystal could be isolated.…”

Heterocyclizations of β-alkoxy, β-diaminoalkyl, and related β-functionalized enones (enals) with NCN-binucleophiles

“…a Yield is given for both regioisomers b Reverse regioselectivity has been also reported[132,133].Scheme 23. 2-(1H-Pyrazol-1-yl)pyrimidine-4-carboxylates 58.…”

“…Enaminone 51 bearing an additional ester group also proved to be a good reagent for the preparation of pyrimidines (Scheme 21); representative examples included acetal 52 [128][129][130] The scope of reported enones included derivative 54 [132,133] decorated with two glyoxylate moieties (Scheme 22) and other polycarbonyl enones 55. An interesting study revealed that their condensation with NCN binucleophiles, e.g.…”