Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation

Synthesis of Quinazolin-4(3H)‑ones via Amidine N‑Arylation

Pyrido[4,3-d]pyrimidin-4(3H)-one (1) was prepared by reacting 2-trifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd2(dba)3 and Xantphos, followed by cyclization effected with HBTU and subsequent demethylation using PhBCl2. The amidine arylation method was found applicable for t...

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Veröffentlicht in:Journal of organic chemistry 2013-02, Vol.78 (3), p.1273-1277
Hauptverfasser: Li, Bryan, Samp, Lacey, Sagal, John, Hayward, Cheryl M, Yang, Christine, Zhang, Zhijun
Format: Artikel
Sprache:eng
Schlagworte:
Amidines - chemistry
Catalysis
Cyclization
Hydrocarbons, Halogenated - chemistry
Molecular Structure
Nicotinic Acids - chemistry
Pyrimidinones - chemical synthesis
Pyrimidinones - chemistry
Quinazolinones - chemical synthesis
Quinazolinones - chemistry
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Zusammenfassung:Pyrido[4,3-d]pyrimidin-4(3H)-one (1) was prepared by reacting 2-trifluoromethyl-4-iodo-nicotinic acid (2) with amidine 9a catalyzed by Pd2(dba)3 and Xantphos, followed by cyclization effected with HBTU and subsequent demethylation using PhBCl2. The amidine arylation method was found applicable for the syntheses of quinazolin-4(3H)-ones. Thus, reaction of 2-bromo or 2-iodo benzoate esters with amdidines afforded substituted quinazolin-4(3H)-ones in 44–89% yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo302515c