107317-70-4Relevant articles and documents
Photomediated ring contraction of saturated heterocycles
Jurczyk, Justin,Lux, Michaelyn C.,Adpressa, Donovon,Kim, Sojung F.,Lam, Yu-Hong,Yeung, Charles S.,Sarpong, Richmond
, p. 1004 - 1012 (2021/08/31)
Saturated heterocycles are found in numerous therapeutics and bioactive natural products and are abundant in many medicinal and agrochemical compound libraries. To access new chemical space and function, many methods for functionalization on the periphery of these structures have been developed. Comparatively fewer methods are known for restructuring their core framework. Herein, we describe a visible light-mediated ring contraction of a-acylated saturated heterocycles. This unconventional transformation is orthogonal to traditional ring contractions, challenging the paradigm for diversification of heterocycles including piperidine, morpholine, thiane, tetrahydropyran, and tetrahydroisoquinoline derivatives. The success of this Norrish type II variant rests on reactivity differences between photoreactive ketone groups in specific chemical environments. This strategy was applied to late-stage remodeling of pharmaceutical derivatives, peptides, and sugars.
REACTION OF TETRAHYDROFUROISOXAZOLES WITH MOLYBDENUM HEXACARBONYL. A NEW ROUTE TO PREPARATION OF 3-SUBSTITUTED TETRAHYDRO- AND DIHYDROFURAN DERIVATIVES
Fisera, Lubor,Goljer, Igor,Jaroskova, Libuse
, p. 1753 - 1760 (2007/10/02)
3-(4-X-Phenyl)-3a,4,6,6a-tetrahydrofuroisoxazoles Ia-If (X = H, CH3, CH3O, Cl, F, C6H5) react with molybdenum hexacarbonyl to give not only the expected cis-3-aroyl-4-hydroxytetrahydrofuran III, but also its trans isomer IV and 3-aroyl-2,5-dihydrof
