Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
The sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)3·2H2O or KMnO4 as stoichiometric oxidants allowed the use of...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.287 |
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| author | Olga A. Storozhenko Alexey A. Festa Delphine R. Bella Ndoutoume Alexander V. Aksenov Alexey V. Varlamov Leonid G. Voskressensky |
| author_facet | Olga A. Storozhenko Alexey A. Festa Delphine R. Bella Ndoutoume Alexander V. Aksenov Alexey V. Varlamov Leonid G. Voskressensky |
| author_sort | Olga A. Storozhenko |
| collection | DOAJ |
| description | The sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)3·2H2O or KMnO4 as stoichiometric oxidants allowed the use of a wide range of nucleophiles, such as nitromethane, (aza)indoles, pyrroles, phenols, pyrazole, indazole and diethyl malonate. The formation of the target compounds presumably proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence. |
| first_indexed | 2024-12-24T01:30:57Z |
| format | Article |
| id | doaj.art-3ddbf0fd44ae41ad9cf87ee87f20e768 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-24T01:30:57Z |
| publishDate | 2018-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-3ddbf0fd44ae41ad9cf87ee87f20e7682022-12-21T17:22:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-12-011413078308710.3762/bjoc.14.2871860-5397-14-287Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridinesOlga A. Storozhenko0Alexey A. Festa1Delphine R. Bella Ndoutoume2Alexander V. Aksenov3Alexey V. Varlamov4Leonid G. Voskressensky5Organic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian FederationOrganic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian FederationOrganic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian FederationDepartment of Chemistry, North Caucasus Federal University, Pushkin st. 1a, 355009 Stavropol, Russian FederationOrganic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian FederationOrganic Chemistry Department, Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian FederationThe sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)3·2H2O or KMnO4 as stoichiometric oxidants allowed the use of a wide range of nucleophiles, such as nitromethane, (aza)indoles, pyrroles, phenols, pyrazole, indazole and diethyl malonate. The formation of the target compounds presumably proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence.https://doi.org/10.3762/bjoc.14.2872-aminochromenedomino reactionimidazo[1,2-a]pyridine2-iminochromeneMichael additionmulticomponent reactionoxidationpyridine amination |
| spellingShingle | Olga A. Storozhenko Alexey A. Festa Delphine R. Bella Ndoutoume Alexander V. Aksenov Alexey V. Varlamov Leonid G. Voskressensky Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines Beilstein Journal of Organic Chemistry 2-aminochromene domino reaction imidazo[1,2-a]pyridine 2-iminochromene Michael addition multicomponent reaction oxidation pyridine amination |
| title | Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines |
| title_full | Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines |
| title_fullStr | Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines |
| title_full_unstemmed | Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines |
| title_short | Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines |
| title_sort | mn mediated sequential three component domino knoevenagel cyclization michael addition oxidative cyclization reaction towards annulated imidazo 1 2 a pyridines |
| topic | 2-aminochromene domino reaction imidazo[1,2-a]pyridine 2-iminochromene Michael addition multicomponent reaction oxidation pyridine amination |
| url | https://doi.org/10.3762/bjoc.14.287 |
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