A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides
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-benzenetetracarboxyl...
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| Format: | Article |
| Language: | English |
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Wiley
2014-01-01
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| Series: | The Scientific World Journal |
| Online Access: | http://dx.doi.org/10.1155/2014/725981 |
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| author | Adrián Ochoa-Terán Jesús Estrada-Manjarrez Marisela Martínez-Quiroz Marco A. Landey-Álvarez Eleazar Alcántar Zavala Georgina Pina-Luis Hisila Santacruz Ortega Luis Enrique Gómez-Pineda José-Zeferino Ramírez Daniel Chávez Julio Montes Ávila Victoria Labastida-Galván Mario Ordoñez |
| author_facet | Adrián Ochoa-Terán Jesús Estrada-Manjarrez Marisela Martínez-Quiroz Marco A. Landey-Álvarez Eleazar Alcántar Zavala Georgina Pina-Luis Hisila Santacruz Ortega Luis Enrique Gómez-Pineda José-Zeferino Ramírez Daniel Chávez Julio Montes Ávila Victoria Labastida-Galván Mario Ordoñez |
| author_sort | Adrián Ochoa-Terán |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-4a22665e48144ea98bfc253f3c533f7a |
| institution | Kabale University |
| issn | 2356-6140 1537-744X |
| language | English |
| publishDate | 2014-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | The Scientific World Journal |
| spelling | doaj-art-4a22665e48144ea98bfc253f3c533f7a2025-02-03T01:31:44ZengWileyThe Scientific World Journal2356-61401537-744X2014-01-01201410.1155/2014/725981725981A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from DianhydridesAdrián Ochoa-Terán0Jesús Estrada-Manjarrez1Marisela Martínez-Quiroz2Marco A. Landey-Álvarez3Eleazar Alcántar Zavala4Georgina Pina-Luis5Hisila Santacruz Ortega6Luis Enrique Gómez-Pineda7José-Zeferino Ramírez8Daniel Chávez9Julio Montes Ávila10Victoria Labastida-Galván11Mario Ordoñez12Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, MexicoDepartamento de Ingeniería Bioquímica, Instituto Tecnológico de Culiacán, 80220 Culiacán, SIN, MexicoCentro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, MexicoCentro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, MexicoFacultad de Ciencias Químico Biológicas, Universidad Autónoma de Sinaloa, 80010 Culiacán, SIN, MexicoCentro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, MexicoDepartamento de Polímeros y Materiales, Universidad de Sonora, 83000 Hermosillo, SON, MexicoCentro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, MexicoDepartamento de Polímeros y Materiales, Universidad de Sonora, 83000 Hermosillo, SON, MexicoCentro de Graduados e Investigación, Instituto Tecnológico de Tijuana, 22510 Tijuana, BC, MexicoFacultad de Ciencias Químico Biológicas, Universidad Autónoma de Sinaloa, 80010 Culiacán, SIN, MexicoCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, 62209 Cuernavaca, MOR, MexicoCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, 62209 Cuernavaca, MOR, MexicoA 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.http://dx.doi.org/10.1155/2014/725981 |
| spellingShingle | Adrián Ochoa-Terán Jesús Estrada-Manjarrez Marisela Martínez-Quiroz Marco A. Landey-Álvarez Eleazar Alcántar Zavala Georgina Pina-Luis Hisila Santacruz Ortega Luis Enrique Gómez-Pineda José-Zeferino Ramírez Daniel Chávez Julio Montes Ávila Victoria Labastida-Galván Mario Ordoñez A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides The Scientific World Journal |
| title | A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides |
| title_full | A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides |
| title_fullStr | A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides |
| title_full_unstemmed | A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides |
| title_short | A Novel and Highly Regioselective Synthesis of New Carbamoylcarboxylic Acids from Dianhydrides |
| title_sort | novel and highly regioselective synthesis of new carbamoylcarboxylic acids from dianhydrides |
| url | http://dx.doi.org/10.1155/2014/725981 |
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