1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines
A simple and efficient one-pot route for the synthesis of novel spiro [indolin– oxadiazol] derivativesby 1,3-dipolar cycloaddition reaction of nitrile oxides and isatin imine under classical or microwave irradiation conditions is described.4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione was...
| Main Author: | |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Iranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECR
2016-02-01
|
| Series: | Iranian Journal of Chemistry & Chemical Engineering |
| Subjects: | |
| Online Access: | http://www.ijcce.ac.ir/article_18804_8c3c2ab41fbe0cd5332c10a4c8541754.pdf |
| _version_ | 1818157968951083008 |
|---|---|
| author | Saeid Souzangarzadeh |
| author_facet | Saeid Souzangarzadeh |
| author_sort | Saeid Souzangarzadeh |
| collection | DOAJ |
| description | A simple and efficient one-pot route for the synthesis of novel spiro [indolin– oxadiazol] derivativesby 1,3-dipolar cycloaddition reaction of nitrile oxides and isatin imine under classical or microwave irradiation conditions is described.4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized by cyclization of thiocarbohydrazide and acetic acid. 3-((3-methyl-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imino)indolin-2-one was prepared by condensation of primary amine of 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione with isatin through a single step and 4'-(3-methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl)- 3'-(substituted phenyl)-4'-hydro spiro[indolin-3,5'[1,2,4]oxadiazol]-2-one were afforded by the reaction of corresponding Schiff base with hydroximinoyl chloride and their derivatives under basic conditions at room temperature. The products were obtained in good yields. Elemental analysis, IR, 1H NMR, 13C NMR, and Mass spectral data confirmed the structure of newly synthesized compounds. |
| first_indexed | 2024-12-11T15:22:38Z |
| format | Article |
| id | doaj.art-a5229784c7814c88858f859b0bb1fc2c |
| institution | Directory Open Access Journal |
| issn | 1021-9986 1021-9986 |
| language | English |
| last_indexed | 2024-12-11T15:22:38Z |
| publishDate | 2016-02-01 |
| 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-a5229784c7814c88858f859b0bb1fc2c2022-12-22T01:00:20ZengIranian Institute of Research and Development in Chemical Industries (IRDCI)-ACECRIranian Journal of Chemistry & Chemical Engineering1021-99861021-99862016-02-013513135188041,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin IminesSaeid Souzangarzadeh0Department of Chemistry, College of Basic Scinences, Yadegar-e-Imam Khomeini (RAH) Shahre- Rey Branch, Islamic Azad University, Tehran, I.R. IRANA simple and efficient one-pot route for the synthesis of novel spiro [indolin– oxadiazol] derivativesby 1,3-dipolar cycloaddition reaction of nitrile oxides and isatin imine under classical or microwave irradiation conditions is described.4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized by cyclization of thiocarbohydrazide and acetic acid. 3-((3-methyl-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)imino)indolin-2-one was prepared by condensation of primary amine of 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione with isatin through a single step and 4'-(3-methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl)- 3'-(substituted phenyl)-4'-hydro spiro[indolin-3,5'[1,2,4]oxadiazol]-2-one were afforded by the reaction of corresponding Schiff base with hydroximinoyl chloride and their derivatives under basic conditions at room temperature. The products were obtained in good yields. Elemental analysis, IR, 1H NMR, 13C NMR, and Mass spectral data confirmed the structure of newly synthesized compounds.http://www.ijcce.ac.ir/article_18804_8c3c2ab41fbe0cd5332c10a4c8541754.pdfspiro indole1,3-dipolar cycloadditionmicrowave irradiationisatin iminesschiff basenitrile oxides |
| spellingShingle | Saeid Souzangarzadeh 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines Iranian Journal of Chemistry & Chemical Engineering spiro indole 1,3-dipolar cycloaddition microwave irradiation isatin imines schiff base nitrile oxides |
| title | 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines |
| title_full | 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines |
| title_fullStr | 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines |
| title_full_unstemmed | 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines |
| title_short | 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides to Isatin Imines |
| title_sort | 1 3 dipolar cycloaddition reaction of nitrile oxides to isatin imines |
| topic | spiro indole 1,3-dipolar cycloaddition microwave irradiation isatin imines schiff base nitrile oxides |
| url | http://www.ijcce.ac.ir/article_18804_8c3c2ab41fbe0cd5332c10a4c8541754.pdf |
| work_keys_str_mv | AT saeidsouzangarzadeh 13dipolarcycloadditionreactionofnitrileoxidestoisatinimines |