An Unexpected Highly Stereoselective Bisaziridination of (E,E)-1,4-Dialkyl-2,3-dinitrobutadienes Followed by a Nitro Group Driven Ring Enlargement

被引：12
作者：
Ciogli, Alessia [2 ]
Fioravanti, Stefania [1 ]
Gasparrini, Francesco [2 ]
Pellacani, Lucio [1 ]
Rizzato, Egon [3 ]
Spinelli, Domenico [3 ]
Tardella, Paolo A. [1 ]
机构：
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
[3] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期
关键词：
SYNTHETIC EXPLOITATION; 1,4-DISUBSTITUTED 2,3-DINITRO-1,3-BUTADIENES; BIS-AZIRIDINE; IN-VITRO; 3,4-DINITROTHIOPHENE; ACCESS; DERIVATIVES; DILTIAZEM; EPOXIDES;
D O I：
10.1021/jo902112j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(+/-)-2,2'-Dinitro-2,2'-biaziridines were obtained by a direct aza-MIRC (Michael initiated ring closure) reaction on (E,E)-1,4-dialkyl-2,3-dinitro-1,3-butadienes under very mild conditions. The reactions occur with high stereoselectivity as shown by the enantioselective HPLC analyses performed on the crude mixtures. Ring enlargement to 3,3'-bi(1,2,4-oxadiazole) derivatives was easily obtained by a simple treatment with sodium iodide in DMSO, with an unforeseen regioselective aziridine C-C cleavage.
引用
收藏
页码：9314 / 9318
页数：5
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