153208-22-1Relevant academic research and scientific papers
Design and Synthesis of Fused Pyridine Building Blocks for Automated Library Generation
Mora-Radó, Helena,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.
, p. 328 - 334 (2021)
We demonstrate that a diboration-electrocyclization sequence provides access to a range of pyridine-fused, small-molecule boronic ester building blocks, and that these are amenable to high-throughput synthesis leading to biaryl and ether-linked compound libraries. Moreover, the implementation of an integrated physicochemical and ADME profiling workflow allows accelerated design of novel lead compounds for application in drug-discovery projects.
Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives
Mora-Radó, Helena,Sotorríos, Lia,Ball-Jones, Matthew P.,Bialy, Laurent,Czechtizky, Werngard,Méndez, María,Gómez-Bengoa, Enrique,Harrity, Joseph P. A.
, p. 9530 - 9534 (2018/07/14)
A range of functionalized heteroaromatic boronic acid derivatives are readily accessed by a diboration/6π-electrocyclization sequence. This study revealed the surprising observation that there is a direct relationship between oxime ether stereochemistry and reactivity towards electrocyclization. Specifically, E-oxime ethers are found to be significantly more reactive than their Z-counterparts (stereochemistry relative to azatriene scaffold). In contrast, the configuration at the azatriene alkene terminus has little impact on reaction rates. Computational analysis offers a rationale for this observation; a Nlone pair→C=C π* orbital interaction lowers the energy of the transition state in the electrocyclization of E-oxime ethers. Finally, unreactive Z-oxime ethers can be converted to the corresponding heterocyclic products by a photolytically promoted E→Z isomerization and electrocyclization sequence.
Pyrazoles, fungicidal compositions and use
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, (2008/06/13)
The invention compounds of formula I STR1 wherein R is H, C1-4 alkyl; optionally substituted aryl or CF3 ; Y is C1-4 alkyl or optionally substituted aryl; A is nitrogen or CH; and Z is optionally substituted hydrocarbyl or
