Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones

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• 作者：Jean-Daniel Malcor ; Yann Brouillette ; Julien Graffion ; Kim Spielmann ; Nicolas Masurier ; Ludovic T. Maillard ; Jean Martinez ; Vincent Lisowski ; ^{vincent.lisowski@univ-montp1.fr" class="auth_mail}
• 关键词：Pyrrolo[d]oxazine-2 ; 4-dione ; Pyrrolodiazepine-2 ; 5-dione ; Diazepines ; Imidazolidine-2 ; 4-dione ; 3-Aminopyrrole derivatives
• 刊名：Tetrahedron
• 出版年：5 August 2014
• 年：2014
• 卷：70
• 期：31
• 页码：4631-4639
• 全文大小：751 K

文摘

A convenient synthesis of pyrrolo[3,2-d][1,3]oxazine-2,4-dione 4 is described and its reactivity towards various nucleophiles studied. The regioselective ring opening of anhydride 4 or its N-alkylated analog 25 in the presence of alanine or proline afforded, respectively, imidazolidinedione 22 and N-protected pyrrolo[3,2-e][1,4]diazepines 30 and 31 in a one-pot process. In a last part of this study, an alternative route to produce a library of eight non protected pyrrolo[3,2-e][1,4]diazepine-2,5-diones 35a–h is described to overcome the limited reactivity of anhydride 4.