The Acid Catalyzed Cleavage of 4-Quinazolylmalonic Ester and Related Compounds to 4-Quinazolone

Abstract

Malonic esters and their substituted derivatives undergo a well-known variety of cleavages under the influence of acidic or basic reagents. As representative of these cleavages the following examples may be cited. When a malonic ester is SUMMARY 1. 4-QuinazoIyImaIonic ester and related compounds have been prepared and found to cleave to 4-quinazolone in acid solution.2. Diethyl ethyl-(2,6-dimethyl-4-pyrimidyl)malonate and ethyl (2,6-dimethyl-4-pyrimidyl)cyanoacetate have been prepared. These compounds undergo hydrolysis and decarboxylation in acid.New York 27, N. Y.

The Scope and Mechanism of Phosphonium-Mediated SNAr Reactions in Heterocyclic Amides and Ureas

“…2-Quinazolin-4-ylmalonic Acid Diethyl Ester (112). Prepared according to the synthesis of 111 : 1 H NMR (400 MHz, CDCl 3 ) δ 13.37 (s, 0.32H), 9.31 (s, 0.58H), 8.10 (d, J = 8.4 Hz, 0.72H), 7.97−7.90 (m, 1.60H), 7.71−7.63 (m, 0.66H), 7.37−7.34 (m, 0.33H), 5.51 (s, 0.63H), 4.33−4.27 (m, 4H), 1.34−1.24 (m, 1H); 13 C NMR (CDCl 3 , 100 MHz) δ 166.7, 162.7, 157.7, 150.8, 148.4, 146.5, 142.3, 134.3, 133.8, 129.8, 128.7, 128.7, 127.3, 126.2, 124.2, 124.1, 119.5, 62.8, 62.0, 61.1, 58.5; HRMS (ESI) calcd for C 15 H 17 N 2 O 4 (M + H + ) 289.1183, found 289.1184.…”