34125-84-3Relevant articles and documents
Studies on the synthesis, stability and conformation of 2-sulfonyl-oxetane fragments
Morgan,Hollingsworth,Bull
, p. 5265 - 5272 (2015/05/13)
2-(Arylsulfonyl)oxetanes have been prepared as new structural motifs of interest for medicinal chemistry. These are designed to fit within fragment space and be suitable for screening in fragment based drug discovery, as well as being suitable for further elaboration or incorporation into drug-like compounds. The oxetane ring is constructed through an efficient C-C bond forming cyclisation which allows the incorporation of a wide range of aryl-sulfonyl groups. Furthermore, biaryl-containing compounds can be accessed through Suzuki-Miyaura coupling from halogenated derivatives. With a number of oxetane containing fragment compounds available, their pH stability was assessed, indicating good half-life values for mono-substituted aryl sulfonyl oxetanes across the pH range (1 to 10). Solubility and metabolic stability data is also reported. Finally, the conformation of the fragments is assessed computationally, providing an indication of possible binding orientations.
On the synthesis of α-amino sulfoxides
Rayner, Peter J.,Gelardi, Giacomo,O'Brien, Peter,Horan, Richard A. J.,Blakemore, David C.
, p. 3499 - 3512 (2014/05/20)
A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successfully prepared and isolated. It is speculated that four other α-amino sulfoxides were synthesised but could not be isolated due to their propensity to α-eliminate the sulfoxide. Ultimately, a stable, cyclic N-Boc α-amino sulfoxide was prepared and this successful synthesis relied on the α-amino sulfoxide being part of a bicyclic [3.1.0] fused ring system that could not undergo α-elimination of the sulfoxide. the Partner Organisations 2014.
ELECTROPHILIC REAGENTS FOR MONOHALOMETHYLATION,THEIR PREPARATION AND THEIR USES
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Page/Page column 16-17, (2012/05/19)
The invention provides a compound of formula A, B, C or D, methods for making them, intermediates therefor, and their use in making organic biologically active compounds: (Formula (A)). Wherein: ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R1, R2, R3, R4, R5, R6, R7, R8, R9, R1O are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates ? Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate; or (Formula (B)). Wherein: X = F, CI, Br, I, sulfonate esters, phosphate esters or other another leaving group; and R1, R2, R3, R4, R5 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino and R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates; and R12 = resin, naphthalene or substituted naphthalene Excluding the case when: X = F and R1= R2 = R3 = R4= R5 = H and R6 = R7 = R8 = R9 = methyl, R10 = H and R11 = triflate or tetrafluoroborate and when X = F and R1= R2 = R3 = R4= R5 = H and R12 = poly(styrene-co- divinylbenzene) and R11 = triflate or tetrafluoroborate; or (Formula (C)). Wehrein ? X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group ? R13 = naphthalene or substituted naphthalene ? R6, R7, R8, R9, R10 are each individually selected from H, alkyl, aryl, alkynyl, alkenyl, cycloalkyl, cycloalkenyl, alcoxy, nitro, halogen or amino; or are selected from H, C1C10 alkyl, aryl, C1C10 alkynyl, C1C10 alkenyl, C1C10 cycloalkyl, C1C10 cycloalkenyl, C1C10 alkoxy, nitro, halogen or amino ? R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates or carbonates: or (Formula (D)) X = F, CI, Br, I, sulfonate esters, phosphate esters or another leaving group R13 = naphthalene or substituted naphthalene R11 = tetrafluoroborate, triflate, halogen, perclorate, sulfates, phosphates carbonates R12 = resin, naphthalene or substituted naphthalene.
