Synthesis of Quinazolines and Imidazo[1,2‐c]quinazolines with the Aid of a Low‐Valent Titanium Reagent.

Abstract

Fused pyrimidine derivativesFused pyrimidine derivatives R 0515 Synthesis of Quinazolines and Imidazo[1,2-c]quinazolines with the Aid of a Low-Valent Titanium Reagent. -A novel reductive cyclization of nitrobenzyl amines (I) or the analogous nitrophenyl imidazoles (IV) in the presence of ortho-esters or aldehydes and ketones is accomplished with the TiCl4/Zn reagent system. Imidazoquinazolines (III), (V) and (VII) are obtained in good yields. -(SHI*, D.; WANG, J.; SHI, C.; RONG, L.; ZHUANG, Q.; HU, H.; Synlett

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

“…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 ). The number of zinc, iron, and copper-catalyzed synthesis of quinazoline and quinazolinone derivatives were decreased when the literature survey was narrowed down to the choice of those reactions, performed specifically under MWI as an unconventional and environmentally benign source of energy, in accordance with the title of this review.…”