TY - JOUR A1 - Bera, Shyamal Kanti A1 - Bhanja, Rosalin A1 - Mal, Prasenjit T1 - DDQ in mechanochemical C–N coupling reactions JF - Beilstein Journal of Organic Chemistry PY - 2022/// VL - 18 SP - 639 EP - 646 SN - 1860-5397 DO - 10.3762/bjoc.18.64 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.18.64 KW - ball mill KW - 1H-benzo[d]imidazole KW - C(sp2)–H amidation KW - DDQ KW - mechanochemistry KW - quinazolin-4(3H)-one N2 - 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. ER -