2009
DOI: 10.1002/jlcr.1658
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Synthesis of a series of carbon‐14 labelled 4‐aminoquinazolines and quinazolin‐4 (3H)‐ones

Abstract: Abstract4‐Aminoquinazolines and quinazolin‐4 (3H)‐ones, both labelled with carbon‐14 in the 4‐position, were prepared from 2‐aminobenzonitrile‐[cyano‐14C] and 2‐aminobenzoic acid‐[carboxy ‐14C] or 2‐amino‐ benzamide‐[carboxy ‐14C], respectively, using rapid, one‐pot procedures under microwave enhanced conditions. Copyright © 2009 John Wiley & Sons, Ltd.

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Cited by 10 publications
(4 citation statements)
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“…Saemian et al obtained the quinazolin-4(3H)-ones-[4-14 C] from 2-aminobenzoic acid-[carboxy- 14 C], formic acid and amine. 37 The reaction performed under microwave condition in the absence of solvent or any dehydrating agents.…”
Section: Quinazolinone Synthesis Via Benzoxazinone Intermediatementioning
confidence: 99%
“…Saemian et al obtained the quinazolin-4(3H)-ones-[4-14 C] from 2-aminobenzoic acid-[carboxy- 14 C], formic acid and amine. 37 The reaction performed under microwave condition in the absence of solvent or any dehydrating agents.…”
Section: Quinazolinone Synthesis Via Benzoxazinone Intermediatementioning
confidence: 99%
“…In this approach, according to the synthetic pathway shown in Scheme , after conversion of potassium [ 14 C]cyanide to [carboxyl‐ 14 C]anthranilic acid 1 , it was converted to [carboxyl‐ 14 C 2 ]dithiosalicylic acid 2 via reaction with sodium nitrite under hydrochloric acid condition and subsequent treatment of the resulted [carboxyl‐ 14 C]diazo solution with sodium disulfide solution. Treatment of [carboxyl‐ 14 C 2 ]dithiosalicyclic acid with zinc dust and glacial acetic acid gave [carboxyl‐ 14 C]thiosalicylic acid 3 .…”
Section: Discussionmentioning
confidence: 99%
“…According to previous structure and activity relationship studies on Atevirdine, the compound 3a was introduced by Hadizadeh and Mehrparvar, in which 1‐(3‐alkylamino‐2‐pyridyl) piperazine part of the molecule was unchanged and 5‐alkoxy‐2‐indolylcarbonyl part of molecule was replaced by benzyl‐2‐alkylthio‐imidazolylcarbonyl moiety 9. To further elucidate the mechanism of action and to support the on‐going metabolism studies, the need arose to synthesize the corresponding carbon‐14 compounds, with the label situated in a biologically stable site 10. In this paper the synthesis of 5‐hydroxymethyl‐2‐mercapto‐1‐benzylimidazole‐[2‐ 14 C] 1 and 5‐(hydroxymethyl)‐1‐benzylimidazole‐[2‐ 14 C] 2 and the conversion of these compounds to the four bis(heteroaryl)piperazines‐[2‐ 14 C]( 3a‐d ) is described (Figure 1).…”
Section: Introductionmentioning
confidence: 99%