Synthesis of novel fused quinazolinone derivatives

Abstract

A four-step synthetic route was developed for the synthesis of novel fused quinazolinones, quinazolino[3,4-a]quinazolinones, and isoinodolo[2,1-a]quinazolino[1,2-c]quinazolineones. Reaction of isatoic anhydride and different amines gave various 2-aminobenzamides. Then, reaction of 2-aminobenzamides with 2-nitrobenzaldehyde followed by the reduction of nitro group afforded 2-(2-aminophenyl)-3-aryl-2,3-dihydroquinazolin-4(1H)-one derivatives. Finally, reaction of the latter compounds with aromatic aldehydes or 2-formylbenzoic acid led to the formation of the corresponding products.

SBA‐15‐Pr‐SO3H catalyzed one‐pot synthesis of indole derivatives via Fischer indole pathway

“…[26] However, the chemical surface modification of SBA-15 has made them more useful and versatile for desired applications. [30,31] In continuation of our efforts to develop synthesis of heterocyclic compounds, [21,[32][33][34][35][36][37][38][39][40] herein, we report a versatile approach to the Fischer indole synthesis using an efficient, user-friendly, and easily recovered catalyst, SBA-15-Pr-SO 3 H in ethanol under reflux conditions (Scheme 1). [30,31] In continuation of our efforts to develop synthesis of heterocyclic compounds, [21,[32][33][34][35][36][37][38][39][40] herein, we report a versatile approach to the Fischer indole synthesis using an efficient, user-friendly, and easily recovered catalyst, SBA-15-Pr-SO 3 H in ethanol under reflux conditions (Scheme 1).…”

“…[27][28][29] In this respect, SiO 2 -Pr-SO 3 H is a versatile modified SBA-15, which has been used for a wide range of organic transformations. [30,31] In continuation of our efforts to develop synthesis of heterocyclic compounds, [21,[32][33][34][35][36][37][38][39][40] herein, we report a versatile approach to the Fischer indole synthesis using an efficient, user-friendly, and easily recovered catalyst, SBA-15-Pr-SO 3 H in ethanol under reflux conditions (Scheme 1).…”

Facile Non‐Transition Metal‐Catalyzed Synthesis of 2‐Thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one Derivatives via One‐Pot Multicomponent Reactions

“…Following our ongoing efforts for the synthesis of quinazolinone derivatives, we hereby, report a method for the synthesis of 3‐alkyl/aryl‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one derivatives . The products are obtained from the multicomponent reaction of isatoic anhydride, aniline and amine derivatives, chloroform and sulfur in the presence of potassium tert ‐butoxide (Scheme ).…”

CuBr‐catalysed one‐pot multicomponent synthesis of 3‐substituted 2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one derivatives

“…Extending the chemistry of quinazolinone and its derivatives and the use of copper as catalyst in the reactions have been a goal of our research group. Following our ongoing efforts for the synthesis of quinazolinone derivatives, herein we report a method for the synthesis of 3‐substituted 2‐thioxo‐2,3‐dihydroquinazolin‐4(1 H )‐one derivatives based on a tandem reaction through the reaction of methyl 2‐bromobenzoate, phenylisothiocyanate and sodium azide in the presence of copper bromide and l ‐proline (Scheme ).…”