A short-cut from 1-acetyl adamantane to 2-(1-adamantyl)pyrroles

被引：15
|
作者：
Trofimov, Boris A. [1 ]
Schmidt, Elena Yu. [1 ]
Zorina, Nadezhda V. [1 ]
Senotrusova, Elena Yu. [1 ]
Protsuk, Nadezhda I. [1 ]
Ushakov, Igor A. [1 ]
Mikhaleva, Al'bina I. [1 ]
Meallet-Renault, Rachel [2 ]
Clavier, Gilles [2 ]
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia
[2] UniverSud, CNRS, ENS, PPSM, F-94230 Cachan, France
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 28期
基金：
俄罗斯基础研究基金会;
关键词：
pyrrole; adamantane; oxime; acetylene; O-vinyloxime; 2-(1-adamantyl)pyrrole;
D O I：
10.1016/j.tetlet.2008.05.023
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The oxime of 1-acetyl adamantane 2 is added to acetylene (KOH/DMSO, 70 degrees C, initial acetylene pressure 13 atm, 30 min) to afford the Corresponding O-vinyl oxime 5 in 80% yield. The latter upon heating (DMSO, 120 degrees C, 1 h) gives 2-(1-adamantyl)pyrrole 3, 1-acetyl adamantane 1, and adamantane (6:31 mass ratio), the yield of the pyrrole 3 being 83% (based on 1-acetyl adamantane 1 consumed). Under harsher conditions (NaOH/DMSO, 130 degrees C, atmospheric pressure of acetylene, 4 h) oxime 2 reacts with acetylene to furnish pyrrole 3, 1-acetyl adamantane 1, 1-vinyl adamantane 9, and adamantane (6:7:3:1 mass ratio), with the isolated yield of pyrrole 3 reaching 34%. Under pressure (NaOH/DMSO, 120 degrees C, initial acetylene pressure 14 atm, 1 h) the same reaction leads to 2-(1-adamantyl)-1-vinylpyrrole 4 and ketone 1 in 48% (based on consumed ketone 1) and 24% yields, respectively. The pyrrole 4 is easily deprotected to the corresponding 1H-pyrrole 3 in 77% yield by treatment (aqueous MeCN) with Hg(OAc)(2) and NaBH4. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4362 / 4365
页数：4
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