Sequential C-N and C-O bond formation in a single pot: synthesis of 2H-benzo[b][1,4]oxazines from 2,5-dihydroxybenzaldehyde and amino acid precursors.
Functionalized β-aryl alanine ester derivatives were found to undergo rapid C-N and C-O bond formation with quinol carbonyl compounds to afford 2H-benzo[b][1,4]oxazines in good to excellent yields. This unprecedented finding reported herein offers a straightforward, highly efficient, and rapid method for the synthesis of 2H-benzo[b][1,4]oxazines.
Department of Medicinal Chemistry, Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India. jiqbal@ilsresearch.org
Javed
J
Iqbal
Neelima D
ND
Tangellamudi
Balakrishna
B
Dulla
Sridhar
S
Balasubramanian
D000596:Amino Acids / Q000138:chemical synthesis*; D001547:Benzaldehydes / Q000737:chemistry*; D048588:Benzoxazines / Q000138:chemical synthesis*; D003500:Cyclization; D006873:Hydroquinones / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000596:Amino Acids; D001547:Benzaldehydes; D048588:Benzoxazines; D006873:Hydroquinones; C112784:2,5-dihydroxybenzaldehyde