Benzoic Acid Catalyzed Annulations of α-Amino Acids and Aromatic Aldehydes Containing an ortho-Michael Acceptor: Access to 2,5-Dihydro-1H-benzo[c]azepines and 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines.
A novel one-pot efficient synthesis of 2,5-dihydro-1H-benzo[c]azepines and 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines from α-amino acids and aromatic aldehydes containing an ortho-Michael acceptor is reported via decarboxylative annulations without metal catalysts in yields of 52-91%. Under microwave irradiation, this protocol provides rapid access to polycyclic ring systems (only 5 min in most cases).
Mi
M
Tang
Lingfeng
L
Tong
Lei
L
Ju
Wanwan
W
Zhai
Yang
Y
Hu
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, and State Key Laboratory of Bioengineering Reactors, East China University of Science & Technology , Shanghai 200237, People's Republic of China.
Xinhong
X
Yu
D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry*; D002384:Catalysis; D008872:Microwaves; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000596:Amino Acids; D001381:Azepines; D019817:Benzoic Acid