Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

Abstract

Oxygenative cleavage of an inert CAr–NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is achieved through an efficient, catalyst free, one step synthesis of 8-benzyloxy, 7-aminoquinoline directly from 8-aminoquinoline in water at room temperature.

Acid Catalyzed Multicomponent Reaction to Access Functionalized N‐Benzhydryl Amides: A Tandem Ritter Reaction

“…[24] Henry-Ritter reactions are reported to access one pot synthesis of N-(β-Nitro) amides from aldehyde, nitro compounds and nitriles. [25] In continuation of our research efforts to explore CÀ H functionalisation reactions for the construction of CÀ C, [26,27] CÀ N [28,29] and CÀ O [30,31] bonds in open flask conditions, we aimed to investigate the one-pot multicomponent reaction for the synthesis of amides. Considering the importance of the complex amide products, we assumed that readily available and less expensive nitriles would be an excellent amidation tool in tandem Ritter reaction.…”

Acid‐Catalyzed Tandem Ritter and Mannich Reactions for Direct Access to 3‐Aryl 3‐amidooxindoles from Isatin

“…[31] J. Zhou et al reported a catalytic Ritter reaction of 3-alkyl and 3-aryl-3-hydroxy oxindoles and nitriles for the synthesis of 3-substituted-3-aminooxindoles (Figure 2). [32] As a part of our ongoing research program on CÀ H functionalizations for the construction of CÀ C [33,34,35] and CÀ N [36,37,38,39] bonds, we became interested in Ritter and Mannich reactions and envisioned that multicomponent Ritter reaction could affect the single step synthesis of diverse and complex 2oxindole derivatives by C3 functionalization of isatin. In this paper, we report the development of novel and efficient acid catalyzed synthesis of variety of sterically crowded diamide products, 3-aryl-3'-amidooxindoles in one pot MCR directly from commercially available isatin, nucleophile, and nitrile (Figure 2).…”

Micelle‐Enabled One‐Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions

“…Neat water or so called “ on‐water ” reaction was first introduced by Sharpless . Since then many elegant reactions have been reported . Although on‐water reactions offer much benefits, wide‐spread adoption has been limited by inability of on‐water reaction to be adapted to all traditional chemical transformation reactions due to heterogeneous behaviour.…”