Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides)
A novel series of indole and quinoline tricarboxamides were synthesized using simple and efficient one-pot pseudo-five-component reactions of 2-formylindole or 2-chloro-3-formyl quinolines, isocyanides, amines, and Meldrum’s acid as a CH-acid in CH2Cl2 at room temperature. This conversion has been a...
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| Format: | Article |
| Language: | English |
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Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR
2018-08-01
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| Series: | Iranian Journal of Chemistry & Chemical Engineering |
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| Online Access: | http://www.ijcce.ac.ir/article_28213_fe78afbfbacb0eb77ccffc182226c60b.pdf |
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| author | Morteza Shiri Majid Mohamed Heravi Vahideh Zadsirjan Atefeh Nejatinezhad-Arani Suhas Ashok Shintre Neil Anthony Koorbanally |
| author_facet | Morteza Shiri Majid Mohamed Heravi Vahideh Zadsirjan Atefeh Nejatinezhad-Arani Suhas Ashok Shintre Neil Anthony Koorbanally |
| author_sort | Morteza Shiri |
| collection | DOAJ |
| description | A novel series of indole and quinoline tricarboxamides were synthesized using simple and efficient one-pot pseudo-five-component reactions of 2-formylindole or 2-chloro-3-formyl quinolines, isocyanides, amines, and Meldrum’s acid as a CH-acid in CH2Cl2 at room temperature. This conversion has been achieved via the construction of new bonds including two C-C bonds, two C-N bonds, and one C=O bond. Remarkably, three peptide bonds were formed through a domino sequence including Knoevenagel reaction, [1+4] cycloaddition, deacetonation and also, aminolysis reaction. Particularly, a number of structurally remarkable and pharmacologically significant products were provided in excellent yields. |
| first_indexed | 2024-12-18T23:57:03Z |
| format | Article |
| id | doaj.art-756c6b05b9af4585929556d78d89a30e |
| institution | Directory Open Access Journal |
| issn | 1021-9986 1021-9986 |
| language | English |
| last_indexed | 2024-12-18T23:57:03Z |
| publishDate | 2018-08-01 |
| publisher | Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR |
| record_format | Article |
| series | Iranian Journal of Chemistry & Chemical Engineering |
| spelling | doaj.art-756c6b05b9af4585929556d78d89a30e2022-12-21T20:46:40ZengIranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECRIranian Journal of Chemistry & Chemical Engineering1021-99861021-99862018-08-0137410111528213Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides)Morteza Shiri0Majid Mohamed Heravi1Vahideh Zadsirjan2Atefeh Nejatinezhad-Arani3Suhas Ashok Shintre4Neil Anthony Koorbanally5Department of Chemistry, Faculty of Science, Alzahra University, Tehran, I.R. IRANDepartment of Chemistry, Faculty of Science, Alzahra University, Tehran, I.R. IRANDepartment of Chemistry, Faculty of Science, Alzahra University, Tehran, I.R. IRANDepartment of Chemistry, Faculty of Science, Alzahra University, Tehran, I.R. IRANSchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, SOUTH AFRICASchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, SOUTH AFRICAA novel series of indole and quinoline tricarboxamides were synthesized using simple and efficient one-pot pseudo-five-component reactions of 2-formylindole or 2-chloro-3-formyl quinolines, isocyanides, amines, and Meldrum’s acid as a CH-acid in CH2Cl2 at room temperature. This conversion has been achieved via the construction of new bonds including two C-C bonds, two C-N bonds, and one C=O bond. Remarkably, three peptide bonds were formed through a domino sequence including Knoevenagel reaction, [1+4] cycloaddition, deacetonation and also, aminolysis reaction. Particularly, a number of structurally remarkable and pharmacologically significant products were provided in excellent yields.http://www.ijcce.ac.ir/article_28213_fe78afbfbacb0eb77ccffc182226c60b.pdf2-formylindole2-chloro-3-formyl quinoloneisocyanidesmeldrum’s acidmulticomponent reactiontricarboxamide |
| spellingShingle | Morteza Shiri Majid Mohamed Heravi Vahideh Zadsirjan Atefeh Nejatinezhad-Arani Suhas Ashok Shintre Neil Anthony Koorbanally Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides) Iranian Journal of Chemistry & Chemical Engineering 2-formylindole 2-chloro-3-formyl quinolone isocyanides meldrum’s acid multicomponent reaction tricarboxamide |
| title | Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides) |
| title_full | Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides) |
| title_fullStr | Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides) |
| title_full_unstemmed | Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides) |
| title_short | Pseudo-Five-Component Condensation for the Diversity-Oriented Synthesis of Novel Indoles and Quinolines Containing Pseudo-Peptides (Tricarboxamides) |
| title_sort | pseudo five component condensation for the diversity oriented synthesis of novel indoles and quinolines containing pseudo peptides tricarboxamides |
| topic | 2-formylindole 2-chloro-3-formyl quinolone isocyanides meldrum’s acid multicomponent reaction tricarboxamide |
| url | http://www.ijcce.ac.ir/article_28213_fe78afbfbacb0eb77ccffc182226c60b.pdf |
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