ChemInform Abstract: Preparation of 2‐Phenyl‐2‐hydroxymethyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline and 2‐Methyl‐4‐oxo‐3,4‐dihydroquinazoline Derivatives Formation.

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Solid-Phase Synthesis of 3-Hydroxy-6-Nitroquinolin-4(1H)-ones with Two Diversity Positions

“…Surprisingly, the already described protocols with polyphosphoric acid, 2-5 trifluoroacetic acid, 6 or N-methylpyrrolidone 3 were not universally applicable. Polyphosphoric acid and N-methylpyrrolidone were unreactive while trifluoroacetic acetic furnished relatively better results: intermediates (6Cd), (6Dd), (6Gd), (6Hd), (6Ca), (6Da), (6Ga), and (6Ha) were successfully cyclized.…”

“…Synthesis of N-methyl and N-phenyl derivatives using rearrangement of the corresponding phenacylanthranilates has been described only once. 3 In our previous article, we described an unsuccessful attempt to synthesize similar derivatives with use of TFA cyclization. 6 Concerning the biological effects, N-alkylated 2-arylhydroxyquinolinones are totally unexplored group of derivatives; hence, they still represent focus our interest.…”

“…In contrast, synthetic derivatives of 3-hydroxyquinolin-4(1H)-ones only became a focus of research attention in the past decade, when a new synthetic route leading to this group of compounds was developed (Scheme 1). 1 The procedure described was later successfully used for the preparation of various hydroxyquinolinones [2][3][4][5] and represents the simplest and also the most widely applicable solution-phase synthesis known so far. In addition, in 2007 the first solid-phase synthesis of hydroxyquinolinone-carboxamides was published 6 taking advantage of the same strategy.…”

Study of anthranilates cyclization to 2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one derivatives and alternative way of their synthesis

“…Comparison of the anthranilates 1 reactivity is summarized in Table 1. In the original paper, 11 the course of the anthranilate cyclisation has been confirmed only with help of NMR characterization of the single prepared product. We managed to prepare two target dihydroquinazolinones in a sufficient crystalline form for X-ray studies and we offer the full structure elucidation of derivatives 3d and 2b' (Figure 1).…”

“…In 2000 a paper describing an interesting use of 2-oxo-2-phenylethyl 2-aminobenzoate for the preparation of dihydroquinazolinone derivative was published. 11 The mentioned ester was heated in acetic acid in a presence of ammonium acetate giving the 2-hydroxymethyl-2-phenyl-2,3-dihydroquinazolin-4(1H)-one instead of the expected 2-(2-aminophenyl)-4-phenyloxazole. When methylammonium acetate was used instead, the corresponding 3-N-methyl derivative was obtained.…”