Switchable solvent-controlled divergent synthesis: an efficient and regioselective approach to pyrimidine and dibenzo[b,f][1,4]oxazepine derivatives

Abstract

An efficient solvent-controlled regioselective reaction has been developed. The reaction represents a novel protocol for the divergent one-pot synthesis of pyrimidine and dihydrodibenzo[b,f][1,4]oxazepine derivatives.

Oxidative Dehydrosulfurative Carbon–Oxygen Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Aryl Alcohols

“…Traditionally, 2-aryloxypyrimidines have been prepared by nucleophilic aromatic substitution or Ullmann-type C–O cross-coupling of pyrimidine possessing (pseudo)­halide at the C2 position with aryl alcohol (Scheme A) . Due to the requirement for multistep synthesis of most of the pyrimidine partners, especially for densely substituted ones, these reaction protocols are limited with respect to rapid diversification.…”

Photoredox Activation of Anhydrides for the Solvent‐Controlled Switchable Synthesis of gem‐Difluoro Compounds**

“…The way chemists approach synthetic organic chemistry is also constantly evolving. Unconventional, yet valuable concepts have been introduced into the field, including but not limited to latestage functionalization, [12] atom economy, [13,14] bifunctional reagents, [15] divergent syntheses, [16][17][18][19][20] and multicomponent reactions. [21] Indeed, these strategies allow scientists to readily access a broader chemical space for achieving synthetic endeavors.…”

Solvent‐Controlled Regioselectivity in Nucleophilic Substitution Reactions of 1‐X‐2,4‐Difluorobenzenes with Morpholine Using Deep Eutectic Solvents

“…al. reported the solvent‐controlled regioselectivity in reactions between pyrimidine and dibenzo[b,f] [1,4] oxazepine derivatives [17] . The limited number of reports on solvent‐controlled substitution reactions is surprising, given the fact that aromatic nucleophilic substitution reactions are known to be sensitive to the choice of reaction medium [18,19] …”

“…reported the solvent-controlled regioselectivity in reactions between pyrimidine and dibenzo[b,f] [1,4] oxazepine derivatives. [17] The limited number of reports on solvent-controlled substitution reactions is surprising, given the fact that aromatic nucleophilic substitution reactions are known to be sensitive to the choice of reaction medium. [18,19] In the past few decades, increasing concerns about the environmental impact of chemical processes has led to the emergence of environmentally benign synthetic strategies, including the use of "green" solvents as an alternative to conventional volatile organic solvents (VOCs).…”