Metal‐ and Catalyst‐Free Electrochemical Synthesis of Quinazolinones from Alkenes and 2‐Aminobenzamides

Abstract

A metal‐ and catalyst‐free electrochemical approach to the preparation of quinazolinones with alkenes and 2‐aminobenzamides via selective anodic oxidative difunctionalization/C−C bond cleavage/cyclization/oxidation has been developed. The synthesis process features convenient operation, low cost, and environmental friendliness, which make it a promising method for the preparation of quinazolinone derivatives.

Quinazolin-4(3H)-ones: A Tangible Synthesis Protocol via an Oxidative Olefin Bond Cleavage Using Metal-Catalyst Free Conditions

“…More recently, Abdullaha et al [61] has reported metal-free, iodine catalyzed reactions to synthesize quinazolinones from o-aminobenzamide and alkynes/alkenes ( Figure 2). Furthermore, a very interesting discovery, metal and catalyst free electrochemical synthesis of quinazolinones from o-aminobenzamide and alkenes was reported by Teng et al [62] (Figure 2).…”

“…In view of our previous knowledge in the advancement of synthetic methodologies [61,62] for quinazolinones synthesis [63,64] and the promising results are shown in the Figure 3, the methodology was further extended to benzothiadiazine-1,1-dioxides synthesis [67] from o-aminobenzenesulfonamide and styrenes (Figure 4, 5a-b). Surprisingly, when o-aminobenzenesulfonamide 4 and different functional group bearing styrenes were subjected to the identical condition as Table 1, the expected product 5 was observed in 60% yield (Figure 4).…”

Electrochemical Synthesis of Quinazolinones by the Metal-Free and Acceptor-Free Dehydrogenation of 2-Aminobenzamides

“…17 Furthermore, in our previous work, we reported an electrochemical metal-free synthesis of quinazolinones by coupling of alkenes with 2-aminobenzamides. 18 We therefore speculated the N-substituted 2-aminobenzamides might undergo dehydrogenation/cyclization through electrocatalytic anodic oxidation. Here, we report an electrochemical synthesis of quinazolinones by coupling of 2-aminobenzamides and halides in one pot.…”

Advances in Electrochemical Decarboxylative Transformation Reactions

“…Catalyst-free electrochemical synthesis has attracted more attention towards CÀCb ond transformation under mild, metal and external oxidantf ree conditions. [23] In 2019, Lei et al reported ac atalyst-free electrochemical decarboxylative crosscoupling of NHP esters with quinoline derivativest oc onstruct the Csp 3 ÀCsp 2 bonds. This strategy is complementary to the Kolbe reaction, and theseC sp 3 radicals provide the opportunities for new kinds of reactions in organic synthesis.…”