A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones
The three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones, 3-formylchromone and anilines under catalyst-free conditions afforded a library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones in good to excellent yields and in a diastereoselective transform...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-02-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.43 |
| _version_ | 1818418149278613504 |
|---|---|
| author | Pitchaimani Prasanna Pethaiah Gunasekaran Subbu Perumal J. Carlos Menéndez |
| author_facet | Pitchaimani Prasanna Pethaiah Gunasekaran Subbu Perumal J. Carlos Menéndez |
| author_sort | Pitchaimani Prasanna |
| collection | DOAJ |
| description | The three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones, 3-formylchromone and anilines under catalyst-free conditions afforded a library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones in good to excellent yields and in a diastereoselective transformation. This transformation generates one C–C and one C–N bond and presumably proceeds via a reaction sequence comprising a Michael-type addition–elimination reaction, a nucleophilic attack of an enamine to a carbonyl reminiscent of one of the steps of the Bayllis–Hilman condensation, and a final deoxygenation. The deoxygenation is assumed to be induced by carbon monoxide resulting from the thermal decomposition of the dimethylformamide solvent. |
| first_indexed | 2024-12-14T12:18:05Z |
| format | Article |
| id | doaj.art-e249e93ec34841c4bd475c24b98164d5 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T12:18:05Z |
| publishDate | 2014-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e249e93ec34841c4bd475c24b98164d52022-12-21T23:01:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-02-0110145946510.3762/bjoc.10.431860-5397-10-43A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-onesPitchaimani Prasanna0Pethaiah Gunasekaran1Subbu Perumal2J. Carlos Menéndez3Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, Tamilnadu, IndiaDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, Tamilnadu, IndiaDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai - 625 021, Tamilnadu, IndiaDepartamento de Química Orgánica and Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, SpainThe three-component domino reactions of (E)-3-(dimethylamino)-1-arylprop-2-en-1-ones, 3-formylchromone and anilines under catalyst-free conditions afforded a library of novel (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4H-chromen-4-ones in good to excellent yields and in a diastereoselective transformation. This transformation generates one C–C and one C–N bond and presumably proceeds via a reaction sequence comprising a Michael-type addition–elimination reaction, a nucleophilic attack of an enamine to a carbonyl reminiscent of one of the steps of the Bayllis–Hilman condensation, and a final deoxygenation. The deoxygenation is assumed to be induced by carbon monoxide resulting from the thermal decomposition of the dimethylformamide solvent.https://doi.org/10.3762/bjoc.10.43chromonesdomino reactionsMichael additionsmulticomponent reactionstransfer hydrogenation |
| spellingShingle | Pitchaimani Prasanna Pethaiah Gunasekaran Subbu Perumal J. Carlos Menéndez A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones Beilstein Journal of Organic Chemistry chromones domino reactions Michael additions multicomponent reactions transfer hydrogenation |
| title | A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones |
| title_full | A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones |
| title_fullStr | A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones |
| title_full_unstemmed | A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones |
| title_short | A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones |
| title_sort | catalyst free multicomponent domino sequence for the diastereoselective synthesis of e 3 2 arylcarbonyl 3 arylamino allyl chromen 4 ones |
| topic | chromones domino reactions Michael additions multicomponent reactions transfer hydrogenation |
| url | https://doi.org/10.3762/bjoc.10.43 |
| work_keys_str_mv | AT pitchaimaniprasanna acatalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT pethaiahgunasekaran acatalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT subbuperumal acatalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT jcarlosmenendez acatalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT pitchaimaniprasanna catalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT pethaiahgunasekaran catalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT subbuperumal catalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones AT jcarlosmenendez catalystfreemulticomponentdominosequenceforthediastereoselectivesynthesisofe32arylcarbonyl3arylaminoallylchromen4ones |