通过若干串联反应合成一些含异喹啉骨架化合物
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摘要
本论文主要利用若干串联反应合成了一些含异喹啉骨架化合物,共由以下部分组成：(1)发展了邻炔基苯甲醛腙、a,β-不饱和羰基化合物与溴的三组分反应,得到了并环的异喹啉类化合物；(2)实现了邻炔基苯甲醛肟与苯炔的串联反应,得到了一系列桥环的异喹啉类化合物。
我们发现,邻炔基苯甲醛腙、α,β-不饱和羰基化合物与溴的三组分串联反应可以很好地进行,并且反应在不同的条件可以得到不同结构的产物。当反应在70℃,以DABCO为碱的条件下,可以一步有效地合成多种取代的异喹啉并吡唑骨架化合物。当反应条件为0℃,K3PO4为碱时,得到的是1,2-二氢异喹啉骨架化合物。
同时,我们还实现了邻炔基苯甲醛肟与苯炔在三氟甲磺酸银催化下的串联环化反应。反应经过分子内环化,[3+2]环加成和重排过程,得到了一种带桥环的异喹啉类化合物。
This dissertation mainly centers on methodology development for the construction of isoquinoline compounds via tandem reactions. It is divided into two parts:(1) three-component reaction of N'-(2-alkynylbenzylidene)hydrazide, a, (3-unsaturated carbonyl compound, with bromine; (2) silver triflate-catalyzed tandem reaction of 2-alkynylbenzaldoxime with aryne.
Different outcomes were generated under different conditions for the three-component reaction of N'-(2-alkynylbenzylidene)hydrazide,α,β-unsaturated carbonyl compound, with bromine.6-BromoH-pyrazolo[5,1-α]isoquinoline was obtained when the reaction was performed in NMP at 70℃in the presence of DABCO as base, while 6-bromo-1,2,3,10b-tetrahydropyrazolo[5,1-α]isoquinoline was afforded when the reaction occurred in DMAc at 10℃in the presence of K3PO4 as base.
In the meantime, a novel and unexpected reaction of 2-alkynylbenzaldoxime with aryne in the presence of silver triflate (10 mol%) under mild conditions was discovered. This reaction proceeded through 6-endo-cyclization, [3+2] cycloaddition and rearrangement, leading to 2-oxa-6-aza-bicyclo[3.2.2]nona-6,8-diene derivatives in moderate to good yields.
我们发现,邻炔基苯甲醛腙、α,β-不饱和羰基化合物与溴的三组分串联反应可以很好地进行,并且反应在不同的条件可以得到不同结构的产物。当反应在70℃,以DABCO为碱的条件下,可以一步有效地合成多种取代的异喹啉并吡唑骨架化合物。当反应条件为0℃,K3PO4为碱时,得到的是1,2-二氢异喹啉骨架化合物。
同时,我们还实现了邻炔基苯甲醛肟与苯炔在三氟甲磺酸银催化下的串联环化反应。反应经过分子内环化,[3+2]环加成和重排过程,得到了一种带桥环的异喹啉类化合物。
This dissertation mainly centers on methodology development for the construction of isoquinoline compounds via tandem reactions. It is divided into two parts:(1) three-component reaction of N'-(2-alkynylbenzylidene)hydrazide, a, (3-unsaturated carbonyl compound, with bromine; (2) silver triflate-catalyzed tandem reaction of 2-alkynylbenzaldoxime with aryne.
Different outcomes were generated under different conditions for the three-component reaction of N'-(2-alkynylbenzylidene)hydrazide,α,β-unsaturated carbonyl compound, with bromine.6-BromoH-pyrazolo[5,1-α]isoquinoline was obtained when the reaction was performed in NMP at 70℃in the presence of DABCO as base, while 6-bromo-1,2,3,10b-tetrahydropyrazolo[5,1-α]isoquinoline was afforded when the reaction occurred in DMAc at 10℃in the presence of K3PO4 as base.
In the meantime, a novel and unexpected reaction of 2-alkynylbenzaldoxime with aryne in the presence of silver triflate (10 mol%) under mild conditions was discovered. This reaction proceeded through 6-endo-cyclization, [3+2] cycloaddition and rearrangement, leading to 2-oxa-6-aza-bicyclo[3.2.2]nona-6,8-diene derivatives in moderate to good yields.
引文
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15. Robinson, R. J. Chem. Soc.1917,111,876.
16. Stavenger, R. A.; Schreiber, S. L. Angew. Chem. Int. Ed.2001,40,3417.
17. Nicolaou, K. C.; Pfefferkom, J. A.; Cao, G. Angew. Chem. Int. Ed.2000,39,734.
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