Diastereoselective T?Reaction of 1?Alkyl-5-(5-nitro-2?N?morpholinobenzylidene) barbituric Acids in the Solid State: Synthesis of 1?Alkyl- 2,4,6-trioxoperhydropyrimidino-5-spiro-10′-(7′-nitro- 1′,3′,4′,9′,10′,10a′-hexahydro-2′-oxa)-4a′-azaphenanthrenes and Their 2′-Thia Analogues

Konstantin A. Krasnov; Victor N. Khrustalev

首页> 外文期刊>Crystal growth & design >Diastereoselective T?Reaction of 1?Alkyl-5-(5-nitro-2?N?morpholinobenzylidene) barbituric Acids in the Solid State: Synthesis of 1?Alkyl- 2,4,6-trioxoperhydropyrimidino-5-spiro-10′-(7′-nitro- 1′,3′,4′,9′,10′,10a′-hexahydro-2′-oxa)-4a′-azaphenanthrenes and Their 2′-Thia Analogues

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Diastereoselective T?Reaction of 1?Alkyl-5-(5-nitro-2?N?morpholinobenzylidene) barbituric Acids in the Solid State: Synthesis of 1?Alkyl- 2,4,6-trioxoperhydropyrimidino-5-spiro-10′-(7′-nitro- 1′,3′,4′,9′,10′,10a′-hexahydro-2′-oxa)-4a′-azaphenanthrenes and Their 2′-Thia Analogues

机译：固态的1？烷基-5-（5-硝基-2？N？吗啉代亚苄基）巴比妥酸的非对映选择性T？反应：合成1？烷基-2,4,6-三氧杂氢嘧啶-5-螺-10'- （7'-硝基-1'，3'，4'，9'，10'，10a'-六氢-2'-氧杂）-4a'-氮杂菲及其2'-硫杂类似物

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1-Alkyl-5-(5-nitro-2-N-morpholinobenzylidene) barbituric acids undergo tert-amino effect reactions (T-reactions) yielding 1-alkyl- 2,4,6-trioxoperhydropyrimidino-5-spiro-10′-(7′-nitro-1′,3′,4′,9′,10′,10a′- hexahydro-2′-oxa)-4a′-azaphenanthrene derivatives as a mixture of (S~*,S~*)- and (S~*,R~*)-diastereomers. A novel heterophase modification of the T-reaction is proposed, which makes it possible to afford nearly pure (S~*,S~*)-diastereomers in high yields, whereas rearrangement reactions in solutions usually lack stereoselectivity. To our best knowledge, this is the first example of deliberate tuning stereodirection of a T-reaction by external conditions. Using X-ray diffraction analysis, we demonstrate that this diastereoselectivity of the solid state T-reaction is due to a peculiar crystal structure of starting 5-arylidene barbiturates, which accommodates only one specific conformation fixed by a strong intramolecular C?H···π interaction.

机译：1-烷基-5-（5-硝基-2-N-吗啉代亚苄基）巴比妥酸经过叔氨基效应反应（T反应）生成1-烷基-2,4,6-三氧杂氢嘧啶基-5-螺基-10'- （7'-硝基-1'，3'，4'，9'，10'，10a'-六氢-2'-氧杂）-4a'-氮杂菲衍生物作为（S〜*，S〜*）的混合物-和（S〜*，R〜*）-非对映异构体。提出了一种新颖的T反应异相修饰方法，该方法可以以高收率获得接近纯的（S〜*，S〜*）非对映异构体，而溶液中的重排反应通常缺乏立体选择性。据我们所知，这是通过外部条件故意调整T反应的立体声方向的第一个示例。使用X射线衍射分析，我们证明了这种固态T反应的非对映选择性是由于起始的5芳基巴比妥酸酯的特殊晶体结构所致，该结构仅容纳由一种强分子内C？H···固定的特定构象。 π相互作用。

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《Crystal growth & design》 |2014年第8期|共8页
作者
Konstantin A. Krasnov; Victor N. Khrustalev;
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中图分类晶体学;
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solutions; conformation; accommodates;

机译：解决方案;构想;适应;

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1. Diastereoselective T?Reaction of 1?Alkyl-5-(5-nitro-2?N?morpholinobenzylidene) barbituric Acids in the Solid State: Synthesis of 1?Alkyl- 2,4,6-trioxoperhydropyrimidino-5-spiro-10′-(7′-nitro- 1′,3′,4′,9′,10′,10a′-hexahydro-2′-oxa)-4a′-azaphenanthrenes and Their 2′-Thia Analogues [J] . Konstantin A. Krasnov, Victor N. Khrustalev Crystal growth & design . 2014,第8期

机译：固态的1？烷基-5-（5-硝基-2？N？吗啉代亚苄基）巴比妥酸的非对映选择性T？反应：合成1？烷基-2,4,6-三氧杂氢嘧啶-5-螺-10'- （7'-硝基-1'，3'，4'，9'，10'，10a'-六氢-2'-氧杂）-4a'-氮杂菲及其2'-硫杂类似物

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