title: A novel and highly regioselective synthesis of new carbamoylcarboxylic acids from dianhydrides.
abstract: A regioselective synthesis has been developed for the preparation of a series of N,N'-disubstituted 4,4'-carbonylbis(carbamoylbenzoic) acids and N,N'-disubstituted bis(carbamoyl) terephthalic acids by treatment of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (1) and 1,2,4,5-benzenetetracarboxylic dianhydride (2) with arylalkyl primary amines (A-N). The carbamoylcarboxylic acid derivatives were synthesized with good yield and high purity. The specific reaction conditions were established to obtain carbamoyl and carboxylic acid functionalities over the thermodynamically most favored imide group. Products derived from both anhydrides 1 and 2 were isolated as pure regioisomeric compounds under innovative experimental conditions. The chemo- and regioselectivity of products derived from dianhydrides were determined by NMR spectroscopy and confirmed by density functional theory (DFT). All products were characterized by NMR, FTIR, and MS.
authors: Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, Mexico.
authors: Adrián
authors: A
authors: Ochoa-Terán
authors: Departamento de Ingeniería Bioquímica, Instituto Tecnológico de Culiacán, 80220 Culiacán, SIN, Mexico.
authors: Jesús
authors: J
authors: Estrada-Manjarrez
authors: Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, Mexico.
authors: Marisela
authors: M
authors: Martínez-Quiroz
authors: Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, Mexico.
authors: Marco A
authors: MA
authors: Landey-Álvarez
authors: Facultad de Ciencias Químico Biológicas, Universidad Autónoma de Sinaloa, 80010 Culiacán, SIN, Mexico.
authors: Eleazar
authors: E
authors: Alcántar Zavala
authors: Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, Mexico.
authors: Georgina
authors: G
authors: Pina-Luis
authors: Departamento de Polímeros y Materiales, Universidad de Sonora, 83000 Hermosillo, SON, Mexico.
authors: Hisila
authors: H
authors: Santacruz Ortega
authors: Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, Mexico.
authors: Luis Enrique
authors: LE
authors: Gómez-Pineda
authors: Departamento de Polímeros y Materiales, Universidad de Sonora, 83000 Hermosillo, SON, Mexico.
authors: José-Zeferino
authors: JZ
authors: Ramírez
authors: Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, Mexico.
authors: Daniel
authors: D
authors: Chávez
authors: Facultad de Ciencias Químico Biológicas, Universidad Autónoma de Sinaloa, 80010 Culiacán, SIN, Mexico.
authors: Julio
authors: J
authors: Montes Ávila
authors: Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, 62209 Cuernavaca, MOR, Mexico.
authors: Victoria
authors: V
authors: Labastida-Galván
authors: Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, 62209 Cuernavaca, MOR, Mexico.
authors: Mario
authors: M
authors: Ordoñez
mesh_terms: D000812:Anhydrides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000812:Anhydrides; D002264:Carboxylic Acids