Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones

Efficient Method for the Synthesis of Benzamides from Benzoic Acids and Aryl Isothiocyanates using K2 HPO4

“…For example, the chloro‐substituted benzoic acid reacted rapidly with different phenyl isothiocyanates to afford the corresponding N ‐aryl benzamides (Table , 3 g‐j ) in good to moderate yields. Similarly, 2‐iodo benzoic acid reacted efficiently with 4‐nitrophenyl isothiocyanate to give the desired benzamides in 65 % yield (Table , 3 k ). These results show that halogens are well tolerated in this reaction, providing a great opportunity for further synthetic manipulations.…”

Synthesis of 2‐(1,2,3‐Triazolyl)benzamide Derivatives by a Copper(I)‐Catalyzed Multicomponent Reaction

“…The generation of aniline from NaN 3 and aryl halide derivatives in the presence of copper salts has been reported by several research groups. For example, Li, Chen, and co‐workers used this phenomenon to synthesize quinazolinones from 2‐iodobenzamide, NaN 3 , and aldehydes. Singh and co‐workers utilized the in situ generated 2‐aminobenzaldehydes, from 2‐bromobenzaldehydes and NaN 3 , in a condensation reaction to prepare the corresponding quinolines in a multicomponent manner Our findings emphasize one of the great features of multicomponent reactions, that is, the utilization of an unstable intermediate.…”

Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from β-Aminoamides and Orthoesters

“…This compound was prepared from 2-aminonicotinamide (126 mg, 0.92 mmol) and triethyl orthobenzoate (309 mg, 312 µL, 1.38 mmol) and acetic acid (165 mg, 158 µL, 2.76 mmol) in absolute ethanol (3 mL) at 110 °C for 12 h. Yield: 164 mg (80%) as an off-white solid, m.p. 181–182 °C (lit [ 35 ] m.p. 178–180 °C); IR (CHCl 3 ): 3210, 1672 cm −1 ; 1 H-NMR (400 MHz, DMSO- d 6 ): δ 12.8 (br s, 1H), 8.99 (dd, J = 4.5, 2.0 Hz, 1H), 8.54 (dd, J = 7.8, 2.0 Hz, 1H), 8.25 (d, J = 8.1 Hz, 2H), 7.67–7.56 (complex, 3H), 7.55 (dd, J = 7.8, 4.5 Hz, 1H); 13 C-NMR (101 MHz, DMSO- d 6 ): δ 163.4, 159.2, 156.6, 155.9, 136.0, 132.9, 132.4, 129.1, 128.5, 122.7, 116.6; HRMS (ESI): m/z for C 13 H 9 N 3 O [M + 1] + : calcd.…”

“…The option of using primary alcohols for this transformation dramatically increased the scope of the synthesis due to the vast array of available substrates. Finally, other methods involved the reaction of lithium 2-(diethylaminocarbonyl)anilide with aryl- and alkylnitriles [ 32 ] as well as various copper [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ] and palladium [ 2 , 41 , 42 , 43 , 44 ] catalyzed heterocyclizations.…”