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One-pot synthesis of quinazolin-4(3H)-ones and fused quinazolinones by a palladium-catalyzed domino process
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-23 , DOI: 10.1016/j.tet.2017.11.060
Zhi-Lin Ren , Han-Han Kong , Wen-Ting Lu , Mei Sun , Ming-Wu Ding

An efficient one-pot synthesis of quinazolin-4(3H)-ones, benzoimidazo[2,1-b]quinazolin-12(6H)-ones and imidazo[2,1-b]quinazolin-5(1H)-ones via a palladium-catalyzed domino process has been developed. The Pd-catalyzed reactions of 2-azidobenzamides 1 with isocyanides 2 produced quinazolin-4(3H)-ones 4 at room temperature by a domino Pd-catalyzed cross-coupling/carbodiimide-mediated cyclization. However, as 2-azido-N-(2-bromophenyl)benzamides 1 were used under heating condition in the presence of Cs2CO3, the benzoimidazo[2,1-b]quinazolin-12(6H)-ones 5 were directly obtained by twice Pd-catalyzed domino cyclization. A domino reogioselective 5-exo-dig intramolecular cyclization reaction of alkynyl-containing azides 6 with isocyanides 2 generated imidazo[2,1-b]quinazolin-5(1H)-ones 9 in 74–93% yields in the presence of catalyst Pd(PPh3)4 and K2CO3.



中文翻译:

钯催化多米诺骨反应一锅法合成喹唑啉-4(3 H)-酮和稠合喹唑啉酮

高效一锅合成喹唑啉-4(3 H)-one,苯并咪唑[2,1 - b ]喹唑啉-12(6 H)-one和咪唑并[2,1 - b ] quinazolin-5(1 H)已经开发了通过钯催化的多米诺骨牌生产的一种。 在室温下,通过多米诺骨牌Pd催化的交叉偶联/碳二亚胺介导的环化作用,Pd催化2-叠氮苯甲酰胺1与异氰酸酯2生成了quinazolin-4(3 H)-ones 4。然而,作为2-叠氮基-N-(2-溴苯基)苯甲酰胺1在加热条件下在Cs 2 CO 3存在下使用。,通过两次Pd催化的多米诺环化反应直接获得苯并咪唑并[2,1 - b ]喹唑啉-12(6 H)-ones 5。多米诺reogioselective 5 -外掏含炔基叠氮化物的分子内环化反应6与异氰化物2生成的咪唑并[2,1- b ]喹唑啉-5(1 ħ) -酮9中74-93%的产率在催化剂存在下Pd(PPh 34和K 2 CO 3

更新日期:2017-11-23
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