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2-氨基-4H-吡喃与N-溴代琥珀酰亚胺的反应。

The reaction of 2-amino-4H-pyrans with N-bromosuccinimide.

作者信息

Samadi Abdelouahid, Silva Daniel, Chioua Mourad, Infantes Lourdes, Soriano Elena, Marco-Contelles José

机构信息

Laboratorio de Química Médica, IQOG (CSIC), Juan de la Cierva, 3, 28006, Madrid, Spain,

出版信息

Mol Divers. 2015 Feb;19(1):103-22. doi: 10.1007/s11030-014-9560-4. Epub 2014 Dec 14.

DOI:10.1007/s11030-014-9560-4
PMID:25502233
Abstract

The reaction of racemic 2-amino-4H-pyrans, such as 3-amino-1-aryl-1H-benzo[f]chromene-2-carbonitriles, with N-bromosuccinimide (NBS), in CH2Cl2, at room temperature, is a very quick, regio, stereoselective, and high yielding process, affording major racemic (1S, 2S)-2-bromo-3-imino-benzo[f]chromene or racemic (1S, 2S)-2-bromo-3-(bromoimino)-benzo[f]chromene derivatives, when using 1.0 or 2.2 equivalents of NBS, respectively. This reaction, extended to isomeric 2-amino-4-aryl-4H-benzo[h]chromene-3-carbonitriles, showed an unexpected reactivity, affording racemic (3S,4S)-3-bromo-2-(bromoimino)-benzo[h]chromene-3-carbonitriles or 2-oxo-2H-benzo[h]chromene-3-carbonitriles, when using 2.2 or 1.0 equivalents of NBS, respectively. The reaction of alkyl 6-amino-5-cyano-2-methyl-4H-pyran-3-carboxylates has yielded unstable racemic (3S,4S)-alkyl 3-bromo-2-(bromoimino)-3-cyano-6-methyl-3,4-dihydro-2H-pyran-5-carboxylates. The mechanism of these reactions has been investigated by computational methods.

摘要

外消旋2-氨基-4H-吡喃（如3-氨基-1-芳基-1H-苯并[f]色烯-2-腈）与N-溴代琥珀酰亚胺（NBS）在二氯甲烷中于室温下反应，是一个非常快速、区域选择性、立体选择性且产率高的过程。分别使用1.0或2.2当量的NBS时，可得到主要的外消旋（1S，2S）-2-溴-3-亚氨基苯并[f]色烯或外消旋（1S，2S）-2-溴-3-（溴亚氨基）苯并[f]色烯衍生物。该反应扩展到异构的2-氨基-4-芳基-4H-苯并[h]色烯-3-腈时，显示出意外的反应活性。分别使用2.2或1.0当量的NBS时，可得到外消旋（3S，4S）-3-溴-2-（溴亚氨基）苯并[h]色烯-3-腈或2-氧代-2H-苯并[h]色烯-3-腈。烷基6-氨基-5-氰基-2-甲基-4H-吡喃-3-羧酸酯的反应生成了不稳定的外消旋（3S，4S）-烷基3-溴-2-（溴亚氨基）-3-氰基-6-甲基-3，4-二氢-2H-吡喃-5-羧酸酯。已通过计算方法研究了这些反应的机理。

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