Iodine-Promoted Oxidative Cyclization of Acylated and Alkylated Derivatives from Epoxides toward the Synthesis of Aza Heterocycles

Abstract

A new method for directly synthesizing acylated and alkylated quinazoline derivatives by the epoxide ring-opening reaction in the presence of I 2 /DMSO with 2-aminobenzamide is described herein. The developed mild protocol is efficient and displays a wide variety of functional group tolerance and substratecontrolled high selectivity, and the application of a continuous flow technique allows for faster reaction time and higher yields. Moreover, the robustness of the method is applicable in gramscale synthesis.

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

“…A noteworthy advancement in this field has been achieved by Jayaram and colleagues in 2023 by synthesising the derivatives of 2‐benzoylquinazolin‐4(3 H )‐one and phenyl‐(pyrrolo[1,2‐a] quinoxalin‐4‐yl) (Scheme 72). [737] These authors have employed a catalytic amounts of molecular iodine in the presence of DMSO at 110 °C to react a series of starting materials for the conversion towards the desired molecules. The synthesis of library of corresponding product has been achieved using styrene oxide derivatives reacting with substituted 2‐aminobenzamides and substituted 2‐(1 H ‐pyrrol‐1‐yl) anilines.…”

Catalyst-free activation of N–C(O) Amide bonds – efficient cascade synthesis of N-acyl thiocarbamides in batch and continuous-flow

“…Despite recent advancements, significant progress has been achieved in continuous-flow chemistry. [56][57][58][59] These methods provide several benefits for sustainable chemical processes, such as operational safety, rapid reactions, improved massand heat-transfer, minimization of reaction volumes, improvement in the degrees of sample-and reagent-mixing and easy scalability, thus offering a potent platform for chemical innovation. 60,61 Hence, our laboratory has focused on developing new methods for selectively cleaving C-N bonds in amides using both batch and continuous-flow processes.…”

A Direct Method for Synthesis of Quinoxalines and Quinazolinones Using Epoxides as Alkyl Precursor

“…In 1966, Cheeseman and Tuck [15] first synthesized pyrrolo [1,2-a]quinoxalines using 1-(2-aminophenyl)-pyrrole as the starting material with aqueous formic acid under reflux conditions. Since then, a number of groups have made tremendous efforts to construct these compounds [16][17][18][19][20][21][22][23][24][25]. In 2022, Ma [16] reported a Cu(II)-catalyzed synthesis of pyrrolo[1,2-a]quinoxalines using N,N-dimethylethanolamine (DMEA) as a C1 synthon.…”

“…In addition, the method of Ma's group was also applicable to the synthesis of quinazolin-4-one and benzo [4,5]imidazoquinazoline. During the preparation of our manuscript, by means of an I 2 -DMSO synergistic system, Lin [17] reported a method for the synthesis of acyl-substituted pyrrolo[1,2-a]quinolines using epoxides as acyl precursors. As part of our research interest in the green synthesis of nitrogen-containing heterocycles under metal-free conditions, PEG-400 [18], DMF [19] and DMSO [20] as carbon synthons have been reported (Scheme 1).…”