手性杂螺烯类似物及含氮杂环化合物的合成研究
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摘要
螺烯是一类邻位稠合非平面结构的化合物，具有螺旋性质，其在光学和电化学方面都表现出优良的性质，可以作为液晶分子，传感器和染料等，随着螺烯化合物研究的不断深入，越来越多的手性螺烯化合物被合成出来，一些功能化的螺烯化合物已被应用在不对称催化、手性分子识别、分子机器等方面，因而对螺烯及其类似物的合成和性质研究已成为有机化学的研究热点之一。本论文主要分为两方面：一、手性杂螺烯类似物的合成及催化；二、杂环化合物的合成研究。
第一部分，以甲氧基取代水杨醛和乙二胺为起始原料合成双亚胺，低价钛作用下双亚胺与固体光气反应，构建了含有甲氧基的氮、氧杂螺烯类似物，利用三溴化硼还原得到相应的螺烯二酚类似物，产率83-89%。
第二部分，我们以手性二苯乙二胺、取代水杨醛或2-羟基萘醛衍生物为起始原料，获得含有特殊官能团的螺烯合成子，以低价钛试剂促进的还原偶联串联反应为关键步骤，一步、方便地构建含氮、氧等杂原子的螺烯类似物骨架，合成一系列结构新颖的新型手性杂[5]螺烯、杂[7]螺烯类似物，其ee值均大于99.9%。化合物的结构经单晶X-射线衍射证明。后经三溴化硼还原，构建了新型手性杂[5]螺烯和杂[7]螺烯二酚类似物，并以此为催化剂，催化了醛与二乙基锌的加成反应，产率在91-98%，ee值在60-78%。
第三部分，以邻羟基(或硝基)芳醛和手性环己二胺为起始原料，先生成手性双亚胺后，在低价钛试剂作用下与固体光气发生还原环化反应，一步构建三个环，生成手性的双苯并噁嗪衍生物，其ee值均大于99.9%。
第四部分，以苯并色烯-3-酮、氨基吡唑衍生物为原料，硅磺酸为催化剂，DMF为溶剂微波促进下合成了具有螺旋性质的苯[5,6]并色烯[4,3-d]并吡啶[3,4-b]并吡唑-3-酮衍生物，当改变反应条件，可以构建苯[5,6]并色烯[2,3-b]并吡啶[4,3-e]并吡唑类化合物。
Helicenes and helicene-like molecules have been regarded as academic curiositybecause they show nonplanar ortho-fused characteristics and exhibit the feature of helicalchirality. With the recent advances in this research area, helicenes and helicene-likemolecules are considered to be potential candidates serving as liquid crystal molecules,sensors, and dyes. They can also be applied in areas of asymmetric catalysis, chiralmolecular recognition, and molecular machinery. Helicene chemistry has grown from thestage of a descriptive field of aesthetic and curious molecules to an important field ofresearch.
This dissertation consisted of two parts. The first one is focused on the synthesis andapplication of chiral hetero-helicene-likes. The second one is the synthesis of heterocycliccompounds.
The first section,2-hydroxybenzaldehydes and diamines were utilized as the startingmaterials, the formed diimines then undergo a reductive-cyclization process withtriphosgene to give the dioxo-diaza-helicene skeleton induced by low-valent titaniumreagent. Then through the conversion of functional groups, the dioxo-diaza-helicene-likecompounds containing hydroxy group have been obtained in83-89%yields by from theircorresponding compounds containing methoxy group in the presence of BBr3.
The second section, chiral diphenyl diamine, substituted salicylaldehyde or2-hydroxy naphthalene aldehyde derivative were used as the starting material, the formeddiimines then undergo a reductive-cyclization process with triphosgene a step, easily togive the chiral dioxo-diaza-helicene-likes, the enantioselectivity of the product was up to99.9%ee. The structures of the products have been determined by the X-raycrystallographic analysis. The desired chiral dioxo-diaza-helicene-like compoundscontaining hydroxy group were obtained in85-90%yields, up to99.9%ee, in addition, the hydroxy dioxo-diaza-helicene-like compound was applications on the asymmetricnucleophilic addition of Et2Zn to aldehydes get ee values60-78%and in the yield91-98%.
In third section,2-hydroxybenzaldehydes (or2-nitrobenzaldehydes) and chiralcyclohexane-1,2-diamine were utilized as the starting materials, the formed diiminespromoted by low-valent titanium reagen, an access to get benzo[5,6][1,3]oxazino[4,3-c]quinoxaline-dione or octahydroquinoxalino[1,2-c:4,3-c']diquinazoline-dione derivatives,the enantioselectivity of the product was up to99.9%ee.
In forth part, a facile microwave irradiation synthesis of the new helicene-likescompounds benzo[5,6]chromeno[4,3-d]-pyrazolo[3,4-b]pyridin-3-one derivatives bybenzo[f]chromen-3-one amino pyrazole derivatives reactived in DMF and with silicon acidas catalyst is described. While benzo[5,6]chromeno[2,3-b]-pyrazolo[4,3-e]pyridinederivatives can be constructed if the reaction conditions have been changed.
第一部分，以甲氧基取代水杨醛和乙二胺为起始原料合成双亚胺，低价钛作用下双亚胺与固体光气反应，构建了含有甲氧基的氮、氧杂螺烯类似物，利用三溴化硼还原得到相应的螺烯二酚类似物，产率83-89%。
第二部分，我们以手性二苯乙二胺、取代水杨醛或2-羟基萘醛衍生物为起始原料，获得含有特殊官能团的螺烯合成子，以低价钛试剂促进的还原偶联串联反应为关键步骤，一步、方便地构建含氮、氧等杂原子的螺烯类似物骨架，合成一系列结构新颖的新型手性杂[5]螺烯、杂[7]螺烯类似物，其ee值均大于99.9%。化合物的结构经单晶X-射线衍射证明。后经三溴化硼还原，构建了新型手性杂[5]螺烯和杂[7]螺烯二酚类似物，并以此为催化剂，催化了醛与二乙基锌的加成反应，产率在91-98%，ee值在60-78%。
第三部分，以邻羟基(或硝基)芳醛和手性环己二胺为起始原料，先生成手性双亚胺后，在低价钛试剂作用下与固体光气发生还原环化反应，一步构建三个环，生成手性的双苯并噁嗪衍生物，其ee值均大于99.9%。
第四部分，以苯并色烯-3-酮、氨基吡唑衍生物为原料，硅磺酸为催化剂，DMF为溶剂微波促进下合成了具有螺旋性质的苯[5,6]并色烯[4,3-d]并吡啶[3,4-b]并吡唑-3-酮衍生物，当改变反应条件，可以构建苯[5,6]并色烯[2,3-b]并吡啶[4,3-e]并吡唑类化合物。
Helicenes and helicene-like molecules have been regarded as academic curiositybecause they show nonplanar ortho-fused characteristics and exhibit the feature of helicalchirality. With the recent advances in this research area, helicenes and helicene-likemolecules are considered to be potential candidates serving as liquid crystal molecules,sensors, and dyes. They can also be applied in areas of asymmetric catalysis, chiralmolecular recognition, and molecular machinery. Helicene chemistry has grown from thestage of a descriptive field of aesthetic and curious molecules to an important field ofresearch.
This dissertation consisted of two parts. The first one is focused on the synthesis andapplication of chiral hetero-helicene-likes. The second one is the synthesis of heterocycliccompounds.
The first section,2-hydroxybenzaldehydes and diamines were utilized as the startingmaterials, the formed diimines then undergo a reductive-cyclization process withtriphosgene to give the dioxo-diaza-helicene skeleton induced by low-valent titaniumreagent. Then through the conversion of functional groups, the dioxo-diaza-helicene-likecompounds containing hydroxy group have been obtained in83-89%yields by from theircorresponding compounds containing methoxy group in the presence of BBr3.
The second section, chiral diphenyl diamine, substituted salicylaldehyde or2-hydroxy naphthalene aldehyde derivative were used as the starting material, the formeddiimines then undergo a reductive-cyclization process with triphosgene a step, easily togive the chiral dioxo-diaza-helicene-likes, the enantioselectivity of the product was up to99.9%ee. The structures of the products have been determined by the X-raycrystallographic analysis. The desired chiral dioxo-diaza-helicene-like compoundscontaining hydroxy group were obtained in85-90%yields, up to99.9%ee, in addition, the hydroxy dioxo-diaza-helicene-like compound was applications on the asymmetricnucleophilic addition of Et2Zn to aldehydes get ee values60-78%and in the yield91-98%.
In third section,2-hydroxybenzaldehydes (or2-nitrobenzaldehydes) and chiralcyclohexane-1,2-diamine were utilized as the starting materials, the formed diiminespromoted by low-valent titanium reagen, an access to get benzo[5,6][1,3]oxazino[4,3-c]quinoxaline-dione or octahydroquinoxalino[1,2-c:4,3-c']diquinazoline-dione derivatives,the enantioselectivity of the product was up to99.9%ee.
In forth part, a facile microwave irradiation synthesis of the new helicene-likescompounds benzo[5,6]chromeno[4,3-d]-pyrazolo[3,4-b]pyridin-3-one derivatives bybenzo[f]chromen-3-one amino pyrazole derivatives reactived in DMF and with silicon acidas catalyst is described. While benzo[5,6]chromeno[2,3-b]-pyrazolo[4,3-e]pyridinederivatives can be constructed if the reaction conditions have been changed.
引文
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