I2/PhNO2 Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides

doi:10.6023/cjoc202109014

Abstract

A simple and efficient protocol for the synthesis of quinazolin-4(3H)-ones from acetophenones and 2-aminobenz- amides mediated by I₂/PhNO₂ has been achieved. The reaction probably involves two C—N bond formations between acetophenones and 2-aminobenzamides followed by C(CO)—C bond oxidative cleavage of acetophenones. Alternatively, a one-pot tandem reaction mediated by I₂/PhNO₂ and CuBr/K₂CO₃ was performed for the synthesis of quinazolin-4(3H)-ones.

Key words: C(CO)—C cleavage, quinazolinone, iodine, annulation, oxidation

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Ruiqin Zhang, Renchao Ma, Qinjiao Fu, Jing Chen, Yongmin Ma. I₂/PhNO₂ Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 854-862.

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References 32

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Entry	Variation from the standard conditions	Yield/%
1	—	72
2	In DMF, DCE, THF, PhCl or EtOH	Trace or 0
3	PhNO₂ (5 mmol)	62
4	PhNO₂ (10 mmol) as the solvent	54
5	No PhNO₂	59
6	I₂ (0.1 mmol)	45
7	80 ℃ instead of 110 ℃	Trace
8	12 h reaction time	60
9	Reaction under N₂ atmosphere	69
10	No PhNO₂ and under N₂ atmosphere	Trace

Entry	Variation from the standard conditions	Yield/%
1	—	72
2	In DMF, DCE, THF, PhCl or EtOH	Trace or 0
3	PhNO₂ (5 mmol)	62
4	PhNO₂ (10 mmol) as the solvent	54
5	No PhNO₂	59
6	I₂ (0.1 mmol)	45
7	80 ℃ instead of 110 ℃	Trace
8	12 h reaction time	60
9	Reaction under N₂ atmosphere	69
10	No PhNO₂ and under N₂ atmosphere	Trace

I₂/PhNO₂介导的芳乙酮C(CO)—C键氧化断裂和2-氨基芳甲酰胺胺化合成喹唑啉-4(3H)-酮

I₂/PhNO₂ Mediated Synthesis of Quinazolin-4(3H)-ones by C(CO)—C Bond Oxidative Cleavage of Acetophenones and Amination with 2-Aminobenzamides

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I2/PhNO2介导的芳乙酮C(CO)—C键氧化断裂和2-氨基芳甲酰胺胺化合成喹唑啉-4(3H)-酮