51892-16-1Relevant articles and documents
Kinetics and Mechanism for Oxime Formation from Pyridine-2-, -3-, and -4-carboxaldehydes
Malpica, A.,Calzadilla, M.,Baumrucker, J.,Jimenez, J.,Lopez L.,et al.
, p. 3398 - 3401 (1994)
Oxime formation from pyridine-2-, -3-, and -4-carboxaldehydes occurs with rate-limiting carbinolamine dehydration under both acidic and neutral conditions.Carbinolamine dehydration of pyridine-2-carboxaldehyde occurs via a transition state bearing a single positive charge, unlike the corresponding reaction for formyl-1-methylpyridinium ion and the reaction under acidic conditions for pyridine-3- and -4-carboxaldehydes.
A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentanedione (DPD) and related compounds as potential modulators of bacterial quorum sensing
Stotani, Silvia,Gatta, Viviana,Medda, Federico,Padmanaban, Mohan,Karawajczyk, Anna,Tammela, P?ivi,Giordanetto, Fabrizio,Tzalis, Dimitrios,Collina, Simona
supporting information, (2018/10/20)
Resistance to antibiotics is an increasingly serious threat to global public health and its management translates to significant health care costs. The validation of new Gram-negative antibacterial targets as sources for potential new antibiotics remains a challenge for all the scientists working in this field. The interference with bacterial Quorum Sensing (QS) mechanisms represents a potentially interesting approach to control bacterial growth and pursue the next generation of antimicrobials. In this context, our research is focused on the discovery of novel compounds structurally related to (S)-4,5-dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule able to modulate bacterial QS in both Gram-negative and Gram-positive bacteria. In this study, a practical and versatile synthesis of racemic DPD is presented. Compared to previously reported syntheses, the proposed strategy is short and robust: it requires only one purification step and avoids the use of expensive or hazardous starting materials as well as the use of specific equipment. It is therefore well suited to the synthesis of derivatives for pharmaceutical research, as demonstrated by four series of novel DPD-related compounds described herein.
Synthesis and characterization of pyridyl propargyloximes
Erenler, Ramazan
experimental part, p. 3546 - 3548 (2012/02/02)
4-Pyridiniumaldoxime and 3-pyridiniumaldoxime are synthesized by the treatment of 4- and 3-pyridinecarboxaldehydes with hydroxylamine hydrochloride, respectively. Methyl triflate salts were obtained by the treatment of methyl triflate with corresponding 4-pyridiniumaldoxime and 4-pyridinecarboxaldehyde O-propragyloxime. The reactions of 4-pyridiniumaldoxime and 3-pyridiniumaldoxime with 3-bromo-l-trimethylsilyl-l-propyne yielded the corresponding pyridinecarboxaldehyde O-propragyloximes. The structures of these products were determined by 1'H, 13C NMR data and X-ray structural analysis.
