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首页> 外文期刊>Beilstein journal of organic chemistry. >Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles
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Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles

机译：通过4-和5-（邻乙烯基苯乙烯基）恶唑的稠合恶唑啉衍生物的光化学方法官能化苯并双环[3.2.1]辛烯结构

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摘要

Novel cis / trans -4- and cis / trans -5-(2-vinylstyryl)oxazoles have been synthesized by Wittig reactions from the diphosphonium salt of α,α’- o -xylene dibromide, formaldehyde and 4- and 5-oxazolecarbaldehydes, respectively. In contrast, trans -5-(2-vinylstyryl)oxazole has been synthesized by the van Leusen reaction from trans -3-(2-vinylphenyl)acrylaldehyde which is prepared from o -vinylbenzaldehyde and (formylmethylene)triphenylphosphorane. The 4- and 5-(2-vinylstyryl)oxazoles afford, by photochemical intramolecular cycloaddition, diverse fused oxazoline-benzobicyclo[3.2.1]octadienes, which are identified and characterized by spectroscopic methods. The photoproducts formed are relatively unstable and spontaneously or on silica gel undergo oxazoline ring opening followed by formation of formiato- or formamido-benzobicyclo[3.2.1]octenone derivatives. On irradiation of 4-(2-vinylstyryl)oxazole small quantities of electrocyclization product, 4-(1,2-dihydronaphthalen-2-yl)oxazole, are isolated and spectroscopically characterized.
机译：通过Wittig反应，由α，α'-邻二甲苯二溴化二膦鎓盐，甲醛以及4-和5-恶唑甲醛合成了新型的顺/反-4-和顺/反-5-（2-乙烯基苯乙烯基）恶唑，分别。相反，反式-5-（2-乙烯基苯乙烯基）恶唑是通过范鲁森反应由反式-3-（2-乙烯基苯基）丙烯醛合成的，反式-3-（2-乙烯基苯基）丙烯醛是由邻-乙烯基苯甲醛和（甲酰基亚甲基）三苯基膦制备的。 4-和5-（2-乙烯基苯乙烯基）恶唑通过光化学分子内环加成反应提供了各种稠合的恶唑啉-苯并双环[3.2.1]辛二烯，并通过分光光度法对其进行了鉴定和表征。所形成的光产物是相对不稳定的，并且自发地或在硅胶上经历恶唑啉开环，然后形成甲酰胺基或甲酰胺基-苯并双环[3.2.1]辛烯酮衍生物。在4-（2-乙烯基苯乙烯基）恶唑的辐射下，分离出少量的电环化产物4-（1,2-二氢萘-2-基）恶唑，并进行了光谱表征。

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