Solid State Organic Chemistry: Efficient Reactions, Remarkable Yields, and Stereoselectivity

Abstract

The most interesting application of chiral Fumio Toda received his B.Sc, (1956), M.Sc. (1958), and D.Sc. (1962 from Osaka University, where he worked with Masazumi Nakagawa. After postdoctoral work at the University of Illinois with Nelson J. Leonard, he joined the faculty of Ehime University as associate professor and was promoted to professor in 1970. His research interests are focused on strained small ring compounds, aliene-acetylene chemistry, solid state chemistry, and inclusion chemistry.

Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400

“…1,2 One of the areas of central attention in this field includes reactions between solids. 3,4 These reactions are not only of interest from an economical point of view, in many cases they also offer considerable synthetic advantages in terms of yield, selectivity and simplicity of the reaction procedure.…”

“…

AbstractAnthranilic acid 1 was reacted with chloroacetyl chloride in dichloromethane containing triethylamine to yield 2-chloromethyl benzo [d] [1,3]oxazin-4-one 2, which on treatment with aromatic amines yielded 2-(chloromethyl)-3-arylquinazolin-4(3H)-one 3. The latter on reaction with nitrogen nucleophiles such as ethyl piperidine-4-carboxylate, morpholine and piperidine-4-one in CH 3 CN containing K 2 CO 3 and catalytic amount of KI under refluxing conditions, gave 1-(4-oxo-3-aryl-3,4-dihydroquinazolin-2-ylmethyl)piperidine-4-carboxylic acid ethyl ester (4), 2-morpholine-4-ylmethyl-3-aryl-3H-quinazolin-4-one (5), 2-(4-oxopiperidine-1-ylmethyl)-3-aryl-3H-quinazolin-4-one (6) respectively.

…”

Silica Supported Fluoroboric Acid: An Efficient and Reusable Heterogeneous Catalyst for Facile Synthesis of 2-Aliphatic Benzothiazoles, Benzoxazoles, Benzimidazoles and Imidazo[4,5-b]pyridines

“…Organic reactions were found to occur efficiently and selectively on the surface of solids. 26 Even in the absence of new chemistry, a surface reaction may be more desirable than a solution counterpart, because the reaction is more convenient to run, or a high yield of product is attained. In recent years, solid acids and supported reagents 27,28 have attracted much attention due to their low toxicity, high catalytic activity, moisture and air tolerance, ease of separation, recyclability and relatively lower costs.…”

Desorption electrospray ionization mass spectrometry for monitoring the kinetics of Baeyer-Villiger solid-state organic reactions

“…Quantitative analyses of relative intensities of the product, made to quantify the reaction degree of typical solid-state organic reaction (SSOR), show a precision with RSDs of around 5% to 12%, though the RSDs for direct analysis of intensities of the reactant or the product in the solid-state are obviously larger. [20,21]. To our knowledge, however, effort focusing on MS monitoring of SSOR has never been discussed heretofore.…”

“…Shortly after the discovery of DESI, a number of ambient ionization MS methods were reported for direct analysis of solid samples, including direct analysis in real time (DART) [14], desorption atmospheric pressure chemical ionization (DAPCI) [15], matrix-assisted laser desorption electrospray ionization (MALDESI) [16], desorption atmospheric pressure photoionization (DAPPI) [17], electrospray-assisted laser desorption/ionization (ELDI) [18], and atmosphericpressure solids analysis probe (ASAP) [19]. All of these MS techniques, as well as DESI-MS, are potentially applicable for direct following solid-state organic reactions (SSORs) [20,21]. To our knowledge, however, effort focusing on MS monitoring of SSOR has never been discussed heretofore.…”