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首页> 外文期刊>Journal of chemical crystallography >Preparation of Spiro[Benzopyran-Isoxazoles] from the Condensation-Cyclization of Oxime 1,4-Dianions with Select Coumarins
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Preparation of Spiro[Benzopyran-Isoxazoles] from the Condensation-Cyclization of Oxime 1,4-Dianions with Select Coumarins

机译：肟，1，4-二价阴离子与精选香豆素的缩合环化反应制备螺[苯并吡喃-异恶唑]

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Arepresentative spiro[benzopyran-isoxazole], 30- (3,4-dimethoxyphenyl)-N,N-diethyl-4-methyl-40H-spiro[2H- 1-benzopyran-2,50-isoxazol]-7-amine 3a, was submitted for single crystal X-ray analysis. It has been prepared by the condensation-cyclization of dilithiated C(α),O-30,40-dimethoxyacetophenone oxime with a substituted coumarin, 7-(diethylamino)-4-methyl-2H-1-benzopyran-2-one. This results from the 1,2-carbonyl addition, Claisen type, of the dilithiated oxime with this coumarin ester carbonyl to afford C-acylated intermediates that were not isolated, but were acid cyclized to the spiro[benzopyran-isoxazoles], a new spiro heterocyclic system. There was no evidence for Michael-type 1,4-addition found during this initial investigation. An indication that the experimental multiple anion procedure is general, has been the preparation of two additional spiro(benzopyran-isoxazoles) 3b and 3c. Crystals of C_(24)H_(28)N_2O_4 3a are triclinic, p1-bar, a = 9.161(2) ?, b = 9.716(2) ?, c = 12.869(3) ?, a = 75.84(3)o, b = 81.03(3)o, γ = 73.96(3)o, Z = 2, V = 1062.5(4) ?~3, R_1 = 0.0539 and wR_2 = 0.1366 for reflections with I[2σ(I).
机译：代表性的螺[苯并吡喃-异恶唑]，30-（3,4-二甲氧基苯基）-N，N-二乙基-4-甲基-40H-螺[2H- 1-苯并吡喃-2,50-异恶唑] -7-胺3a，被提交用于单晶X射线分析。它是通过二取代的C（α），O-30,40-二甲氧基苯乙酮肟与取代的香豆素7-（二乙氨基）-4-甲基-2H-1-苯并吡喃-2-酮的缩合环化反应制得的。这是由于用该香豆素羰基羰基加成了二锂化肟的1,2-羰基克莱森型，得到了C-酰化的中间体，该中间体未分离，但被酸环化成螺环[苯并吡喃-异恶唑]，一种新的螺环杂环系统。在最初的调查中，没有发现迈克尔型1,4加成的证据。制备另外两种螺（苯并吡喃-异恶唑）3b和3c的实验表明，实验性多阴离子方法是通用的。 C_（24）H_（28）N_2O_4 3a的晶体是三斜晶的，p1-bar，a = 9.161（2）α，b = 9.716（2）α，c = 12.869（3）α，a = 75.84（3）o ，对于I [2σ（I）的反射，b ＝ 81.03（3）o，γ＝ 73.96（3）o，Z ＝ 2，V ＝ 1062.5（4）α〜3，R_1 ＝ 0.0539，wR_2 ＝ 0.1366。

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