1961
DOI: 10.1021/jo01070a046
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The Reaction of Nitriles with o-Aminonitriles: A Convenient Synthesis of Fused 4-Aminopyrimidines1a,b

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Cited by 42 publications
(16 citation statements)
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“…towards nitriles. 14 The formation of pyrazoles 4, and 5 was confirmed by their 1 H NMR spectra where the signals at highest chemical shift (δ≈10-13 ppm), corresponding to the N-H in the intermediates 1 and 2, were replaced by signals at δ≈6-7 ppm, assigned to the NH 2 group of the pyrazoles. The expected pattern for the substituted phenyl ring was observed.…”
Section: Resultsmentioning
confidence: 92%
“…towards nitriles. 14 The formation of pyrazoles 4, and 5 was confirmed by their 1 H NMR spectra where the signals at highest chemical shift (δ≈10-13 ppm), corresponding to the N-H in the intermediates 1 and 2, were replaced by signals at δ≈6-7 ppm, assigned to the NH 2 group of the pyrazoles. The expected pattern for the substituted phenyl ring was observed.…”
Section: Resultsmentioning
confidence: 92%
“…Among other methods encountered in literature, the cyclization of aromatic or aliphatic nitriles with 2-aminobenzonitrile was a frequent reaction that performed in various conditions to afford the 4-aminoquinazolines. In one of them that performed in a nearly neutral condition, despite the prolonged heating at elevated temperatures, the cyclization gave low yields of 2-alkyl and 2-aryl derivatives [18]. Strong bases [19] and acids [20] proved to facilitate the reaction; however, there are scarce examples of synthesis of the 2-alkyl derivatives in basic conditions.…”
Section: Resultsmentioning
confidence: 99%
“…towards nitriles. 14 The formation of pyrazoles 4, and 5 was confirmed by their 1 The presence of cyano groups was confirmed by two bands in their IR spectra, e.g.υ 2240 and 2224 cm -1 for compound 4a.…”
Section: Scheme 2 Synthesis Of Compounds 3 4 Andmentioning
confidence: 92%