Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process.
A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.
Chulabhorn Research Institute, Laksi, Bangkok 10210, Thailand. jumreang@cri.or.th
Jumreang
J
Tummatorn
Charnsak
C
Thongsornkleeb
Somsak
S
Ruchirawat
Tanita
T
Gettongsong
D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D002264:Carboxylic Acids; D011804:Quinolines