Recyclable Itaconic Acid with Water as Green Catalytic System: Synthesis of Substituted 1,5‐Benzodiazepine Derivatives at Room Temperature

Abstract

The construction of new C-N chemical bonds through cocondensation reaction in water media as sole solvent, especially without the use of any metal catalyst has undergoes green protocols. Herein, we describe a water-mediated and metal-free mild protocol for easily accessing of structurally and electronically diverse 1,5-benzodiazepine analogous by using biode-gradable naturally occurring itaconic acid (20 mol%) in 30 minutes with excellent yields. The simplicity in reaction operation, reusability of the catalytic system and simple filtration to get the desired product make this reaction as "green synthetic pathway" upto multi gram scale level.

Synthetic aspects of 1,4- and 1,5-benzodiazepines usingo-phenylenediamine: a study of past quinquennial

“…Tamuli and co-workers 61 developed an eco-friendly methodology for the synthesis of 1,5-BZDs ( 12 ) using itaconic acid as a green catalyst from OPD ( 1 ) and ketones ( 10 ) in water solvent at RT. The authors examined a large substrate scope and prepared 30 derivatives in good to excellent yields (61–95%).…”

NiFe2O4@SiO2@PrNH2–DPA–CeCl3: a cerium-based magnetic nano dual-acid catalyst with high efficacy and recyclability for domino sequential synthesis of lactam ring-fused 1,5-benzodiazepines

“…A speculated mechanism [61][62][63] to account for the synthesis of aryl-substituted lactam ring-fused 1,5-benzodiazepines via domino three-component reaction catalyzed by NiFe 2 O 4 @SiO 2 @PrNH 2 -DPA-CeCl 3 is illustrated in Scheme 3. In the overview of the whole reaction process, the magnetic nano dual-acid catalyst NiFe 2 O 4 @SiO 2 @PrNH 2 -DPA-CeCl 3 plays successive roles in activating carbonyl and imine.…”

Ferrocene anchored activated carbon as a versatile catalyst for the synthesis of 1,5-benzodiazepines via one-pot environmentally benign conditions

“…29 There also exist reports on ferrocene catalyzed C–H imidation of arenes. 33 Ferrocene-based ionic liquid supported catalysts have also been explored for the synthesis of naphthopyran derivatives. 34 However, to the best of our knowledge, ferrocene/activated carbon has not been reported for its application in synthesis of benzodiazepine derivatives by condensation of OPDA with ketones (aromatic and aliphatic).…”

“…28 However, very few reports exist demonstrating the use of ferrocene-based catalysts for organic transformations. [30][31][32][33][34] Pucheault et al reported borylation of diazonium salts in the presence of catalytic amounts of ferrocene. 30 Ferrocene was also used as a catalyst for decarboxylative cross coupling with toluene by Mao and group.…”