Cobalt(II) Chloride Catalyzed one Pot Synthesis of 2-substituted and 3-substituted-4(3H)- Quinazolinones

Abstract

Cobalt(II) chloride (10mol%) was found to be an efficient catalyst for one pot synthesis of variety of 2-substituted-4(3H)quinazolinones by condensation of anthranilamide and aldehydes and synthesis of 3-substituted-4(3H)quinazolinones by condensation of anthranilic acid, orthoester, primary amines at reflux giving good to excellent yields (75-95%).

Comparative study between the Titanium Phosphate TiP2O7 and the Phosphate Fertilizers in the catalysis of the Quinazolin-4(3H)-one derivatives synthesis

“…Na2MoO4.2H2O CH3CN/70°C 9 h 25 18 The obtained results show that the MAP, DAP, TSP, and TiP2O7 are more efficient than other catalysts presented in Table 6. Indeed, their application led to obtaining a higher yield of products in short reaction time.…”

“…Due to the importance of quinazolin-4(3H)-one derivatives, several processes for their Synthesis were developed in the presence or absence of the catalyst. Indeed, the quinazolin-4(3H)-one derivatives were previously synthesized by the thermolysis of 3-arylideneamine-1,2,3-benzotriazine-4-ones in paraffin oil at 300°C 13 or condensation of anthranilamide with aldehydes, ketones or isatoic anhydride with ammonium acetate using various catalysts such as ionic liquid [BDBIm]Br 14 , Sc(OTf)3 15 , TiCl4-Zn 16 , FeCl3.6H2O 17 , Ni(NO3)3.3H2O 18 , CuCl2 in ethanol 19 , p-toluenesulfonic acid/DDQ 20 and SbCl3 under microwave irradiation 21 . Recently different catalysts were reported, such as sulfated MOF-808 22 , H3PO3 23 , FeCl3.6H2O-H2O/PEG-400 24 , Cu@PEI-MGO 25 and Pd(PPh3)4 26 .…”

Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media

“…Cobalt(II) chloride (CoCl 2 , 10 mol%) catalyzed the one-pot threecomponent reaction of anthranilic acid, TEOF, and anilines in CH 3 CN at 70 C to obtain 3-substituted-quinazolin-4(3H)ones. [493][494][495] Both electron-donating and electron-withdrawing anilines provided the products in good yields (75-95%). 495 Quinazolin-4(3H)-ones (618) could also be obtained in good yields via the novel reductive cyclization of o-nitrobenzamides (617) and TEOF (5), promoted by TiCl 4 /Zn in reuxing THF (Scheme 186).…”

“…[493][494][495] Both electron-donating and electron-withdrawing anilines provided the products in good yields (75-95%). 495 Quinazolin-4(3H)-ones (618) could also be obtained in good yields via the novel reductive cyclization of o-nitrobenzamides (617) and TEOF (5), promoted by TiCl 4 /Zn in reuxing THF (Scheme 186). 496 The cyclocondensation of 6-hydrazino-substituted benzimidazo[1,2-c]quinazolines (619) with orthoesters (5, 6, 7) was Scheme 190 The synthesis of thiosaccharides and 1-thiotrehaloses.…”

Copper Nitrate Trihydrate Catalyzed Efficient One Pot Synthesis of Amidoalkylnaphthol Derivatives.

“…Cu(NO 3 ) 2 .3H 2 O has been extensively used as a mild catalyst for a variety of organic trans formations. [34,35b,37-40] In continuation of our work to develop new organic transformations, [34][35][36][37] we would like to report a highly efficient route for the synthesis of amidoalkylnaphthol derivatives by one pot multi component-coupling of β-naphthol, aldehydes, amides/urea catalyzed by commercially available, inexpensive, mild Cu(NO 3 ) 2 .3H 2 O as catalyst in good to excellent yields. (Scheme-1)…”