Copper in Efficient Synthesis of Aromatic Heterocycles with Single Heteroatom

Abstract

Aromatic heterocycles are important structural units in various naturally occurring compounds. Its abundance has drawn attention of synthetic chemists for decades. In the current scenario, new methodologies employing cheap transition metal reagents are highly desirable for efficient and practical synthesis of heterocyclic compounds. In this review article, strategies to synthesize aromatic heterocycles by inexpensive copper reagents have been discussed.

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

“…Although the aforementioned reactions are considered as the most important transition-metal catalyses, a plethora of vital reactions can be effectively catalyzed by various transition metals including reductive elimination, oxidative addition, and transmetallation. Transition metal catalysis has also found extensive applications in the convenient and efficient synthesis of a wide variety of heterocyclic systems (Ma et al, 2017 ; Ramanathan and Liu, 2017 ; Tiwari and Bhanage, 2017 ; Chatterjee et al, 2018 ; Saikia et al, 2018 ; Chen et al, 2020 ; Debabrata et al, 2020 ; Ghosh et al, 2020 ; Janardhanan et al, 2020 ; Jiang et al, 2020 ; Kanwal et al, 2020 ; Kojima and Matsunaga, 2020 ; Li and Zhang, 2020 ; Nagata and Obora, 2020 ; Neto and Zeni, 2020a , b ; Pal et al, 2020 ; Ratmanova et al, 2020 ; Sahiba and Agarwal, 2020 ; Sonawane et al, 2020 ; Xuan et al, 2020 ). However, the literature survey revealed only an example of zinc (Shi et al, 2004 ), a limited number of iron-catalyzed (Melvin et al, 1992 ; Valderrama et al, 1999 ; Kanth et al, 2006 ; Yin et al, 2012 ; Gopalaiah et al, 2017 , 2019 ; Raut and Bhanage, 2017 ; Eidi et al, 2018 ), and relatively more copper-catalyzed reactions, leading to the synthesis of quinazoline and quinazolinone derivatives (Melvin et al, 1992 ; Chatterjee et al, 2018 ; Potuganti et al, 2018 ; Liang et al, 2019 ; Rodrigues et al, 2019 ; Donthiboina et al, 2020 ).…”

An overview of recent advances in the catalytic synthesis of substituted pyrans

“…Multicomponent reactions (MCRs) are the most significant tools for the syntheses of bioactive complex molecules from easily available precursors in excellent yields with good purity in less reaction time and with high atom economy and maximum selectivity. [1][2][3][4] In recent times, development of MCRs using green, cost-efficient catalysts is in high demand in organic synthesis as catalysts play an important role in preventing environmental pollution. Enhancing catalytic activity with high selectivity and efficient recyclability is the main basis of catalytic research.…”

Synthesis of disubstituted furans catalysed by [(AuCl)2(μ-bis(phosphino)metallocene)] and Na[BArF24]

“…While the gold-catalysed formation of furans from alkynes is hardly new, most of the known examples involve intramolecular ring-closing reactions. 57–62 The copper-catalysed synthesis of furans is also known 63 including a report of the [2 + 2 + 1] cycloaddition of a terminal alkyne and acetic anhydride. 64 …”