Synthesis of New 5-Aryl-benzo[ f ][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization
A series of eight new 5-aryl-benzo[ ][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi⁻three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophil...
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| Published in: | Molecules (Basel, Switzerland) Vol. 23; no. 8; p. 2029 |
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| Main Authors: | , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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| Abstract | A series of eight new 5-aryl-benzo[
][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi⁻three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[
][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[
][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before. |
|---|---|
| AbstractList | A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before. A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi⁻three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before. A series of eight new 5-aryl-benzo[ f ][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[ f ][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[ f ][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before. A series of eight new 5-aryl-benzo[ ][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi⁻three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[ ][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[ ][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before. |
| Author | Segura-Olvera, Daniel García-Sánchez, Miguel A Vázquez-Vera, Óscar Gutiérrez-Carrillo, Atilano Rincón-Guevara, Mónica A Ibarra, Ilich A Islas-Jácome, Alejandro Lomas-Romero, Leticia González-Zamora, Eduardo |
| AuthorAffiliation | 2 Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico; mudo-2@hotmail.com (D.S.-O.); agrmn@xanum.uam.mx (A.G.-C.); mags@xanum.uam.mx (M.A.G.-S.) 3 Departamento de Biotecnología, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico; monicarinconguevara@gmail.com 1 Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Av. Acueducto de Guadalupe S/N, Barr. La Laguna Ticomán, Gustavo A Madero C.P. 07340, Ciudad de México, Mexico; vaveos@yahoo.com.mx 4 Laboratorio de Fisicoquímica y Reactividad de Superficies, Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior S/N, Ciudad Universitaria, Coyoacán C.P. 04510, Ciudad de México, Mexico; argel@unam.mx |
| AuthorAffiliation_xml | – name: 1 Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Av. Acueducto de Guadalupe S/N, Barr. La Laguna Ticomán, Gustavo A Madero C.P. 07340, Ciudad de México, Mexico; vaveos@yahoo.com.mx – name: 2 Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico; mudo-2@hotmail.com (D.S.-O.); agrmn@xanum.uam.mx (A.G.-C.); mags@xanum.uam.mx (M.A.G.-S.) – name: 3 Departamento de Biotecnología, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico; monicarinconguevara@gmail.com – name: 4 Laboratorio de Fisicoquímica y Reactividad de Superficies, Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior S/N, Ciudad Universitaria, Coyoacán C.P. 04510, Ciudad de México, Mexico; argel@unam.mx |
| Author_xml | – sequence: 1 givenname: Óscar surname: Vázquez-Vera fullname: Vázquez-Vera, Óscar email: vaveos@yahoo.com.mx organization: Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Av. Acueducto de Guadalupe S/N, Barr. La Laguna Ticomán, Gustavo A Madero C.P. 07340, Ciudad de México, Mexico. vaveos@yahoo.com.mx – sequence: 2 givenname: Daniel surname: Segura-Olvera fullname: Segura-Olvera, Daniel email: mudo-2@hotmail.com organization: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. mudo-2@hotmail.com – sequence: 3 givenname: Mónica A surname: Rincón-Guevara fullname: Rincón-Guevara, Mónica A email: monicarinconguevara@gmail.com organization: Departamento de Biotecnología, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. monicarinconguevara@gmail.com – sequence: 4 givenname: Atilano surname: Gutiérrez-Carrillo fullname: Gutiérrez-Carrillo, Atilano email: agrmn@xanum.uam.mx organization: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. agrmn@xanum.uam.mx – sequence: 5 givenname: Miguel A surname: García-Sánchez fullname: García-Sánchez, Miguel A email: mags@xanum.uam.mx organization: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. mags@xanum.uam.mx – sequence: 6 givenname: Ilich A orcidid: 0000-0002-8573-8033 surname: Ibarra fullname: Ibarra, Ilich A email: argel@unam.mx organization: Laboratorio de Fisicoquímica y Reactividad de Superficies, Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior S/N, Ciudad Universitaria, Coyoacán C.P. 04510, Ciudad de México, Mexico. argel@unam.mx – sequence: 7 givenname: Leticia surname: Lomas-Romero fullname: Lomas-Romero, Leticia email: llr@xanum.uam.mx organization: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. llr@xanum.uam.mx – sequence: 8 givenname: Alejandro orcidid: 0000-0003-0975-5904 surname: Islas-Jácome fullname: Islas-Jácome, Alejandro email: aij@xanum.uam.mx organization: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. aij@xanum.uam.mx – sequence: 9 givenname: Eduardo orcidid: 0000-0002-3995-9126 surname: González-Zamora fullname: González-Zamora, Eduardo email: egz@xanum.uam.mx organization: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Ciudad de México, Mexico. egz@xanum.uam.mx |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30110915$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.3390/molecules15129298 10.1016/j.cbpa.2005.04.003 10.1007/s007060170 10.1038/nprot.2007.71 10.1248/cpb.22.485 10.1039/C6OB01985D 10.1016/S0065-2725(06)91004-6 10.1039/C5SC02913A 10.1039/C7OB02305G 10.1021/jo800745a 10.1002/ejoc.200700340 10.1002/chin.200819137 10.1351/PAC-CON-08-07-03 10.1007/BF03249069 10.1016/S0040-4020(01)00905-X 10.1021/acs.orglett.5b00544 10.1002/chin.200334255 10.1016/S0065-2725(08)60053-7 10.1016/j.tetlet.2012.07.011 10.1002/anie.200460548 10.1039/b104317j 10.1016/j.bmc.2017.08.030 10.1002/chem.201002046 10.1021/jo00099a014 10.1088/1742-6596/79/1/012042 10.1071/CH9942129 10.1016/j.tetlet.2011.07.134 10.1021/ja017563a 10.1016/j.cbpa.2010.03.003 |
| ContentType | Journal Article |
| Copyright | 2018. This work is licensed under https://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2018 by the authors. 2018 |
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| Keywords | multicomponent reactions aromatization benzo[f][1,7]naphthyridines one-pot procedures aza-Diels-Alder cycloadditions microwave assisted synthesis cascade processes |
| Language | English |
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][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process... A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process... A series of eight new 5-aryl-benzo[ f ][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot... |
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| Title | Synthesis of New 5-Aryl-benzo[ f ][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization |
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