THE SYNTHESIS OF ALKYLKETODIHYDROQUINAZOLINES FROM ANTHRANILIC NITRILE.¹

Abstract

BOCERT AND GOTTHELF have already shownZ that ketodihydroquinazolines may be prepared by heating together in sealed tubes anthranilic acid, or its acyl derivatives, with a nitrile, and the reactions there suggested in explanation of this synthesis, taking the case where an acylanthranilic acid was the starting-point, were as follows: /NH. CO. CH, /NH. CO. CH,

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

“…The Radziszewski reaction is an organic reaction which involves the oxidation of nitriles using alkaline hydroperoxide (Radziszewski, 1885 ). Performing the reaction on o -amidobenzonitriles may result in the formation of quinazolin-4-(3 H )-ones (Bogert and Hand, 1902 ). The Radziszewski reaction as a useful and efficient strategy has been employed in the synthesis of quinazolinones under MW conditions.…”

Progress in Synthesis of Pyrazolopyrimidinone

“…邻酰胺基吡唑甲腈的 Bogert-Hand 反应 [99] 被广泛 用来合成吡唑并嘧啶酮 [32] . 1958 年, Cheng 和 Robins [32] 直接用取代 5-酰胺基-4-吡唑甲腈(60)在氢氧化钠-过氧 化氢体系中加热得到化合物 62 (Eq.…”

Synthesis of 2,3-Disubstituted Quinazolinone Derivatives Using Silver Triflate as a Efficient Catalyst at Room Temperature

“…Several methods for the synthesis of 4(3H)-quinazolinones have been investigated in the past. Some common methods include the condensation of 2-aminobenzamides and substituted benzoyl chlorides or their equivalents in ionic liquids (Potewar et al, 2005;Wang et al, 2012), the tandem condensation and C-N cross coupling of 2-halobenzoicacids and amidines (Zhang et al, 2009), the cyclization of o-acylaminobenzamides (Armarego, 1979), 2-aminobenzonitrile (Bogert, Hand, 1902), N-aryl orthanilamides (Stephen, Wadge, 1956;Segarra et al, 1998), nitroenes (Akazome, 1995), and aza-Wittig reactions of a-azido-substituted aromatic imides (Takeuchi et al, 1989;Takeuchi et al, 1991). However, benzyl chlorides are carcinogenic alkylating agents and poisonous lachrymators and the base K2CO3 is needed to neutralize the hydrochloride produced during the reaction (Adib et al, 2011).…”