115147-80-3Relevant articles and documents
Reactions of Nicotinic Acid 1-Oxide with Propionic, Phenylacetic and Benzoic Anhydrides
Nagano, Hiroyuki,Nawata, Yoshiharu,Hamana, Masatomo
, p. 4093 - 4100 (2007/10/02)
Nicotinic acid 1-oxide (1) reacts with hot propionic anhydride to give 4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone 4-oxide (2), 5-aza-3-methyl-4-propionyloxyisocoumarin (3), 4-aza-3-ethyl-3-propionyloxy-1(3H)-isobenzofuranone (4), 4-aza-3-ethyl-3,5-dipropionyloxy-1(3H)-isobenzofuranone (5) and a mixture of 2- and 6-hydroxynicotinic acids (6 and 7).Product 2 is a 2-propionylation product of 1, and 3, 4 and 5 arise from further action of the anhydride on 2.Phenylacetic anhydride undergoes oxidative decarboxylation with 1 to give benzaldehyde and nicotinic acid.The reaction of 1 with benzoic anhydride affords a 2-benzoylation product 4-aza-3-benzoyloxy-3-phenyl-1(3H)-isobenzofuranone 4-oxide (12).Keywords - nicotinic acid 1-oxide; 4-aza-1(3H)-isobenzofuranone 4-oxide; 5-azaisocoumarin; propionic anhydride; phenylacetic anhydride; benzoic anhydride; 2-propionylation; 2-benzoylation; deoxygenative β-propionyloxylation; oxidative decarboxylation