Tandem Hydroformylation/Reductive Amination of 3‐Allyl‐2‐methylquinazolin‐4(3H)‐one |
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Authors: | Yaser A El‐Badry Ahmed F El‐Farargy Peter Eilbracht |
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Institution: | 1. Organic Chemistry Lab, Faculty of Education, Ain Shams University, 11566 Abbasseya, Cairo, Egypt;2. Organic Chemistry Dept., Faculty of Science, Zagazig University, Zagazig, Egypt;3. Organic Chemistry Dept., Faculty of Chemistry, Dortmund Technological University, DE‐Dortmund |
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Abstract: | The 3‐allyl‐2‐methylquinazolin‐4(3H)‐one ( 1 ), a model functionalized terminal olefin, was submitted to hydroformylation and reductive amination under optimized reaction conditions. The catalytic carbonylation of 1 in the presence of Rh catalysts complexed with phosphorus ligands under different reaction conditions afforded a mixture of 2‐methyl‐4‐oxoquinazoline‐3(4H)‐butanal ( 2 ) and α,2‐dimethyl‐4‐oxoquinazoline‐3(4H)‐propanal ( 3 ) as products of ‘linear’ and ‘branched’ hydroformylation, respectively (Scheme 2). The hydroaminomethylation of quinazolinone 1 with arylhydrazine derivatives gave the expected mixture of (arylhydrazinyl)alkyl]quinazolinones 5 and 6 , besides a small amount of 2 and 3 (Scheme 3). The tandem hydroformylation/reductive amination reaction of 1 with different amines gave the quinazolinone derivatives 7 – 10 . Compound 10 was used to prepare the chalcones 11a and 11b and pyrazoloquinazolinones 12a and 12b (Scheme 4). |
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Keywords: | Quinazolin‐4(3H)‐one Hydroformylation/reductive amination Rhodium complexes Pyrazolo‐quinazoline Catalysis |
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