DDQ in mechanochemical C–N coupling reactions
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) condi...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.64 |
| _version_ | 1828333302938861568 |
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| author | Shyamal Kanti Bera Rosalin Bhanja Prasenjit Mal |
| author_facet | Shyamal Kanti Bera Rosalin Bhanja Prasenjit Mal |
| author_sort | Shyamal Kanti Bera |
| collection | DOAJ |
| description | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp2)–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3H)-one derivatives in high yields. |
| first_indexed | 2024-04-13T21:18:08Z |
| format | Article |
| id | doaj.art-ea31d1f792204e01aded8e09a8456e01 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-13T21:18:08Z |
| publishDate | 2022-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-ea31d1f792204e01aded8e09a8456e012022-12-22T02:29:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-06-0118163964610.3762/bjoc.18.641860-5397-18-64DDQ in mechanochemical C–N coupling reactionsShyamal Kanti Bera0Rosalin Bhanja1Prasenjit Mal2School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha 752050, India 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp2)–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3H)-one derivatives in high yields.https://doi.org/10.3762/bjoc.18.64ball mill1h-benzo[d]imidazolec(sp2)–h amidationddqmechanochemistryquinazolin-4(3h)-one |
| spellingShingle | Shyamal Kanti Bera Rosalin Bhanja Prasenjit Mal DDQ in mechanochemical C–N coupling reactions Beilstein Journal of Organic Chemistry ball mill 1h-benzo[d]imidazole c(sp2)–h amidation ddq mechanochemistry quinazolin-4(3h)-one |
| title | DDQ in mechanochemical C–N coupling reactions |
| title_full | DDQ in mechanochemical C–N coupling reactions |
| title_fullStr | DDQ in mechanochemical C–N coupling reactions |
| title_full_unstemmed | DDQ in mechanochemical C–N coupling reactions |
| title_short | DDQ in mechanochemical C–N coupling reactions |
| title_sort | ddq in mechanochemical c n coupling reactions |
| topic | ball mill 1h-benzo[d]imidazole c(sp2)–h amidation ddq mechanochemistry quinazolin-4(3h)-one |
| url | https://doi.org/10.3762/bjoc.18.64 |
| work_keys_str_mv | AT shyamalkantibera ddqinmechanochemicalcncouplingreactions AT rosalinbhanja ddqinmechanochemicalcncouplingreactions AT prasenjitmal ddqinmechanochemicalcncouplingreactions |