1,10‐Phenanthroline‐Catalyzed Tandem Reaction of 2‐Iodoanilines with Isothiocyanates in Water

Abstract

The 1,10-phenanthroline-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water is described, which provides an environmentally benign, efficient and simple route for the preparation of 2-aminobenzothiazoles. The present tandem process shows broad substrate scope in the absence of transition metals and phase-transfer catalysts.

Sodium Hydroxide Catalyzed N-Alkylation of (Hetero) Aromatic Primary Amines and N1,C5-Dialkylation of 4-Phenyl-2-aminothiazoles with Benzyl Alcohols

“…2-Aminobenzothiazoles and thiazoles are versatile synthetic intermediates and are widely used in the synthesis of various biologically active compounds. − In particular, N -alkylated thiazoles and benzothiazoles exhibit different pharmacological and physiological activities. , As a result, much attention has been paid to the synthesis of these compounds. − By considering the importance of 2-aminobenzothiazole derivatives, we investigated herein the N -alkylation of 2-aminobenzothiazoles, and the method has been extended to other heteroaromatic amines including pyridine, pyrimidine, and pyrazines with various alcohols. Under these conditions, we found the N 1 ,C 5 -dialkylation of 4-phenyl-2-aminothiazoles, and there were no reports found for this type of transformation.…”

Phenanthroline‐Decorated Covalent Organic Framework for Catalytic Synthesis of 2‐Aminobenzothiazoles in Water

“…Although various synthetic methods have been developed for their synthesis, the cross‐coupling of 2‐haloarylamines with isothiocyanates has been recognized as a powerful and efficient route [9] . On the other hand, several types of catalysts, including transition metal catalysts, [11–15] organic catalysts, [16] metal organic framework (MOFs), [17] nano metal particles [18] and porous aromatic framework materials (PAFs), [19] have been successfully employed to promote such cross‐coupling reaction. Also, recent studies revealed that the 1,10‐phenanthroline (Phen) played a central role in the process of formation of 2‐aminobenzothiazoles [14–16,19,20] …”

“…On the other hand, several types of catalysts, including transition metal catalysts, [11–15] organic catalysts, [16] metal organic framework (MOFs), [17] nano metal particles [18] and porous aromatic framework materials (PAFs), [19] have been successfully employed to promote such cross‐coupling reaction. Also, recent studies revealed that the 1,10‐phenanthroline (Phen) played a central role in the process of formation of 2‐aminobenzothiazoles [14–16,19,20] …”

Copper/N,N,N′,N′‐Tetramethylethylenediamine‐Catalyzed Synthesis of N‐Substituted Benzoheterocycles via CS Cross‐ Coupling at Ambient Temperature in Water

“…Recently, Ding’s group has realized the synthesis of 2‐imino‐1,3‐oxathioles in water with 37% yield in the presence of an inexpensive base, and in this reaction, high temperature and N 2 protection were necessary 9a. We have developed a transition metal‐free synthesis of 2‐aminobenzothiazoles from 2‐iodoanilines and isothiocyanates using Phen as catalyst in water 9b. Cai et al.…”