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Tandem Hydroformylation/Reductive Amination of 3‐Allyl‐2‐methylquinazolin‐4(3 H )‐one
Author(s) -
ElBadry Yaser A.,
ElFarargy Ahmed F.,
Eilbracht Peter
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200237
Subject(s) - chemistry , hydroformylation , reductive amination , quinazolinone , olefin fiber , amination , carbonylation , catalysis , medicinal chemistry , organic chemistry , tandem , rhodium , carbon monoxide , materials science , composite material
The 3‐allyl‐2‐methylquinazolin‐4(3 H )‐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(4 H )‐butanal ( 2 ) and α ,2‐dimethyl‐4‐oxoquinazoline‐3(4 H )‐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 ).