Synthesis, characterization, and X-ray analysis of new N,N¡ä-disubstituted-1,4-diazepanes

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• 作者：Pedro I. Ramirez-Montes ; Mar¨ªa Eugenia Ochoa ; Vianey Rodr¨ªguez ; Rosa Santillan ; H¨¦ctor Garc¨ªa-Ortega ; Patricia Rodr¨ªguez ; Norberto Farf¨¢n
• 关键词：PGYHHQOTPQLFNH-UHFFFAOYSA-N ; CBAQFWJDFBRRHK-UHFFFAOYSA-N ; IQBCMCZCVBDANU-IAGOWNOFSA-N ; UQKIIFGHOLZFRD-RTBURBONSA-N ; PETMEXRLFIZTKP-RTBURBONSA-N ; PDYAITFLDZPQEL-RTBURBONSA-N ; DHOJIKGRDLATEH-NHCUHLMSSA-N ; YOMLDAWRLGGLQP-NHCUHLMSSA-N ; JUSRKFWOROVLNK-UHFFFAOY
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：31 October, 2012
• 年：2012
• 卷：53
• 期：44
• 页码：5887-5890
• 全文大小：532 K

文摘

The synthesis and structural characterization of six 1,4-diazepanes prepared by condensation of 2,2¡ä-(1,3-propanediyldiimino)diphenols with glyoxal or 2,3-butanedione to give bisbenzoxazolidines and subsequent reduction with BH₃-DMS is reported. The new 1,4-diazepanes were obtained in yields between 75 % and 83 % and characterized by NMR, IR, and HRMS. In addition, the crystal structure analysis showed that the seven-membered ring in 1,4-diazepanes (12a, 12e, and 12d) and bisbenzoxazolidines (11a, 11c, 11f) adopt in all cases twisted chair conformation. Compounds 12a and 12e show disorder in the seven member ring, as a result of the conformational flexibility of the seven-membered ring.