6 research outputs found
A Study of an 8-Aminoquinoline-Directed C(sp(2))-H Arylation Reaction on the Route to Chiral Cyclobutane Keto Acids from Myrtenal
This work outlines a synthetic route that can be used to access chiral cyclobutane keto acids with two stereocenters in five steps from the inexpensive terpene myrtenal. Furthermore, the developed route includes an 8-aminoquinoline- directed C(sp(2))-H arylation as one of its key steps, which allows a wide range of aryl and heteroaryl groups to be incorporated into the bicyclic myrtenal scaffold prior to the ozonolysis-based ringo-pening step that furnishes the target cyclobutane keto acids. This synthetic route is expected to find many applications connected to the synthesis of natural product-like compounds and small molecule libraries
Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry
Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns
A Two-Step Procedure for the Overall Transamidation of 8‑Aminoquinoline Amides Proceeding via the Intermediate <i>N</i>‑Acyl-Boc-Carbamates
Herein
a two-step strategy for achieving overall transamidation
of 8-aminoquinoline amides has been explored. In this protocol, the
8-aminoquinoline amides were first treated with Boc<sub>2</sub>O and
DMAP to form the corresponding <i>N</i>-acyl-Boc-carbamates,
which were found to be sufficiently reactive to undergo subsequent
aminolysis with different amines in the absence of any additional
reagents or catalysts. To demonstrate the utility of this approach,
it was applied on a number of 8-aminoquinoline amides from the recent
C–H functionalization literature, enabling access to a range
of elaborate amide derivatives in good to high yields
Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group
In this preprint, we present our initial results
concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and
alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline
directing group. Efficient C–H alkenylation was
achieved with a wide range of vinyl iodides bearing different aliphatic,
aromatic and heteroaromatic substituents, to furnish the corresponding C3
alkenylated products in good to high yields. In addition, we were able show
that this protocol can also be used to install an alkynyl group into the pyrrolidine
scaffold, when a TIPS-protected alkynyl bromide was used as the reaction
partner. Furthermore, two different methods for the removal of the 8-aminoquinoline
auxiliary are reported, which can enable access to both cis- and trans-configured
carboxylic acid building blocks from the C–H alkenylation products.</p
Base-catalysed F-18-labelling of trifluoromethyl ketones. Application to the synthesis of F-18-labelled neutrophil elastase inhibitors
A new method for the fluorine-18 labelling of trifluoromethyl ketones has been developed. This method is based on the conversion of a-COCF3 functional group to a difluoro enol silyl ether followed by halogenation and fluorine-18 labelling. The utility of this new method was demonstrated by the synthesis of fluorine-18 labelled neutrophil elastase inhibitors, which are potentially useful for detection of inflammatory disorders.De tre första författarna delar förstaförfattarskapet.</p