Fischer Reaction with 2‐Perfluoroalkylated Cyclic Imines ― An Efficient Route to 2‐Perfluoroalkyl‐Substituted Tryptamines and Their Derivatives and Homologues

Abstract

MALDI mass‐spectrometry measurements are combined with self‐consistent mean‐field (SCF) calculations to detect and predict ligand phase separation on Ag nanoparticles. The experimental and theoretical techniques complement each other by enabling quantification of the nearest‐neighbor distribution of a ligand mixture in a monolayer shell. By tracking a characteristic metallic fragment family, analysis of a MALDI spectrum produces a frequency distribution corresponding to specific ligand patterning. Inherent to the SCF calculation is the enumeration of local interactions that dictate ligand assembly. Interweaving MALDI and SCF facilitates a comparison between the experimentally and theoretically derived frequency distributions as well as their deviation from a well‐mixed state. Thus, we combine these techniques to detect and predict phase separation in monolayers that mix uniformly or experience varying degrees of de‐mixing, including microphase separation and stripe formation. Definition of MALDI removed as this is a commonly recognized technique.

Potent, Selective, Water Soluble, Brain-Permeable EP2 Receptor Antagonist for Use in Central Nervous System Disease Models

“…Requisite amines 7a – e (Supporting Information (SI), Figure 1) were synthesized using the known methods, , and they were individually coupled with 23 in the presence of DMAP and EDCI·HCl at 50 °C to furnish the final products 24a – e (Scheme ). Similarly, compound 24f was synthesized using acid 23 and 2-trifluroindole-3-ethanolamine ( 7f ), which was in turn prepared form 2-vinyl-pyrrolidin-2-one (SI Figure 1). Moreover, the compound 2-(2-methylpyrazolo­[1,5- a ]­pyridin-3-yl)­ethan-1-amine ( 7g ) has been synthesized starting from amino-pyridinium iodide (SI Figure 1).…”

2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp3)–H Functionalization of Trifluoroacetimidoyl Chlorides

“…These are largely based on the modification of an existing indole ring − and require a stoichiometric amount of an electrophilic trifluoromethylating reagent such as Togni’s or Umemoto’s reagent (Scheme ). Reports on the Fischer indole synthesis using perfluoroalkylated substrates, as well as other cyclization strategies, are known . However, in many cases, one requires either prefunctionalized starting materials or regioselectivity issues pose important limitations, along with the frequent use of protective groups.…”

Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch

“…As a synthetic strategy, this [3 + 2] annulation affords, in a single operation, the structurally rigid 6-5-5 tricyclic subunit with a substituent at the 3-position of the indole nucleus, which is the basic structure of pharmaceutically valuable natural products. 4 Besides, this nonclassical approach provides access to functionalized pyrroloindoline systems with substitution patterns that are otherwise inaccessible using tryptamines 17 as precursors.…”