171119-05-4Relevant articles and documents
Fast-Synthesis of α-Phosphonyloxy Ketones as Drug Scaffolds in a Capillary Microreactor
Ramanjaneyulu, Bandaru T.,Vidyacharan, Shinde,Yim, Se Jun,Kim, Dong-Pyo
supporting information, p. 7730 - 7734 (2019/12/24)
A simple, room temperature approach for the fast single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, has been developed which involves highly reactive species i.e., 1,2-dicarbonyls that readily react with trialkyl phosphites and formic acids in batch as well as in continuous-flow with the flow rate of 3 ml/min (tR = ～4 s). The present approach reduced the synthesis time from hours to minutes in batch, which was further lowered to a few seconds precisely controlled by single capillary microfluidics. A wide range of 1,2-dicarbonyl derivatives were smoothly transformed to their corresponding α-phosphonyloxy ketones in moderate to good yields (50–82 %) under optimized flow-reaction conditions. Further, the α-phosphonyloxy ketones produced can be utilized in batch process to form benzoin, oxazole core, and α,α′-diarylated carbonyl compounds in 82 %, 50 %, and 54 % yields, respectively, which are alternative key precursors/scaffolds of natural products and active pharmaceutical ingredients (APIs).
Activity of 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines to Tetrahymena
Kaspersen, Svein Jacob,Hoff, Bard Helge,Sundby, Eirik,Charnock, Colin
, p. 35 - 41,7 (2020/07/30)
A series 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines (43 compounds), some of which are epidermal growth factor tyrosine kinase inhibitors, were tested for their protozoal toxicity using an environmental Tetrahymena strain as model organism. The protozoacidal activity of the analogues was found to be highly dependent on a 4-hydroxyl group at the 6-aryl ring, and a chiral 1-phenylethanamine substituent in position 4. Further, the potency was affected by the aromatic substitution pattern of the phenylethanamine: the unsubstituted, the meta-fluoro and the para-bromo substituted derivatives had the lowest minimum protozoacidal concentrations (8-16 μg/mL). Surprisingly, both enantiomers were found to have high potency suggesting that this compound class could have several modes of action. No correlation was found between the compounds protozoacidal activity and the in vitro epidermal growth factor receptor tyrosine kinase inhibitory potency. This suggests that the observed antimicrobial effects are related to other targets. Testing towards a panel of kinases indicated several alternative modes of action.
A sustainable byproduct catalyzed domino strategy: Facile synthesis of α-formyloxy and acetoxy ketones via iodination/nucleophilic substitution/hydrolyzation/oxidation sequences
Zhu, Yan-Ping,Gao, Qing-He,Lian, Mi,Yuan, Jing-Jing,Liu, Mei-Cai,Zhao, Qin,Yang, Yan,Wu, An-Xin
supporting information; experimental part, p. 12700 - 12702 (2012/01/03)
The sustainable byproduct catalyzed domino strategy has been performed for the facile synthesis of α-formyloxy and acetoxy ketones via iodination/nucleophilic substitution/hydrolyzation/oxidation sequences from simple and readily available aromatic ketone
One-pot synthesis of α-formyloxy ketones from enolizable ketones
Kumar, Sunil,Kumar, Ashok,Gupta, Rakesh K.,Kumar, Devinder
, p. 338 - 345 (2008/04/01)
One-pot synthesis of α-formyloxy tones as well as α-acetoxy ketones from enolizable ketones and [hydroxy(tosyloxy) iodo] benzene (HTIB)/polymer supported [hydroxy(tosyloxy) iodo] benzene (PSHTIB) in N,N-dimethylformamide (DMF)/N, N-dimethylacetamide (DMA)
Synthesis of α-acetoxy and formyloxy ketones by thallium(III) promoted α-oxidation
Lee,Jin,Choi
, p. 956 - 957 (2007/10/03)
Treatment of ketones with thallium(III) triflate in amide solvents at 60°C for 30 min followed by addition of small amounts of H2O cleanly provided the corresponding α-acyloxy ketones.
A convenient method for the conversion of halides to alcohols
Alexander,Renyer,Veerapanane
, p. 3875 - 3881 (2007/10/03)
The displacement of halides in unactivated primary bromides and iodides, allylic and benzylic primary and secondary bromides, and primary and secondary α-bromoketones by formate, using triethylammonium formate as the formylating agent, followed by acid or base catalyzed hydrolysis has been found to be an efficient method for the conversion of halides to alcohols.
α-Formyloxycarbonyl Compounds from the Anodic Oxidation of Enol Carbonates
Barba, Fructuoso,Quintanilla, M. Gloria,Montero, Guillermo
, p. 5658 - 5660 (2007/10/03)
Enol carbonates previously synthesized were anodically oxidized yielding the coresponding α-formyloxycarbonyl derivatives with participation of the DMF, used as solvent.
