Studies on synthesis of heterocycles and carbocycles by sequential reactions using unsaturated esters
Studies on synthesis of heterocycles and carbocycles by sequential reactions using unsaturated esters
批准号:
23550054
负责人:
YAMAZAKI SHOKO
金额:
$3.33万
依托单位国家:
日本
项目类别:
Grant-in-Aid for Scientific Research (C)
财政年份:
2011
资助国家:
日本
项目状态:
已结题
起止时间:
2011 至 2013
中文摘要
以高活性α,β-不饱和酯为原料,通过顺序键的形成,开发了一种新的高效的环化反应。不饱和酯如三甲酸乙酯、2-膦酸甲酯和2-三氟甲基丙烯酸酯与偶氮二甲酸二乙酯和PPh3反应生成了吡唑啉类化合物。烯丙基三羧酸酯和酰胺类化合物与TiCl4、TiBr4和AlCl3等Lewis酸反应,高产率地立体选择性地合成了3,4-反式卤代甲基2-氧代四氢呋喃和吡咯烷衍生物。通过NOE实验确定了其立体化学组成。(E)/(Z)-2-丁烯酯与AlCl3或FeCl3反应生成3,4-反式-4-(1-氯乙基)四氢-2-氧代呋喃非对映异构体。(E)/(Z)-2-丁烯基和2-戊烯基酰胺与锌离子反应得到3,4-反式-4-(1-碘乙基和丙基)四氢-2-氧代吡咯烷非对映异构体,这些反应是合成潜在有用化合物的有效途径。
英文摘要
New efficient cyclization reactions using highly reactive alfa,beta-unsaturated esters by sequential bond formations has been developed.The reaction of unsaturated esters such as ethenetricarboxylates, 2-phosphonoacrylate and 2-(trifluoromethyl)acrylate with diethyl azodicarboxylate and PPh3 gave pyrazolines efficiently. Reaction of allyl ethenetricarboxylates and the amides with Lewis acids such as TiCl4, TiBr4 and AlCl3 gave 3,4-trans-halogenomethyl 2-oxotetrahydrofuran and pyrrolidine derivatives stereoselectively in high yields. The stereochemistries were determined by NOE experiments. Reaction of (E)/(Z)-2-butenyl esters with AlCl3 or FeCl3 gave 3,4-trans 4-(1-chloroethyl) tetrahydro-2-oxofuran diastereoisomers stereospecifically. Reaction of (E)/(Z)-2-butenyl and 2-pentenyl amides with ZnI2 gave 3,4-trans 4-(1-iodoethyl and propyl) tetrahydro-2-oxopyrrolidine diastereoisomers stereospecifically.These reactions represent efficient ways to construct potentially useful compounds.
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エテントリカルボン酸アミドの環化反応における官能基選択性
乙烯基三甲酰胺环化反应中的官能团选择性
DOI:
--
发表时间:
2014
期刊:
影响因子:
--
作者:
[山崎祥子, 新名麻美子, 藤浪謙]
通讯作者:
藤浪謙
Lewis acid-promoted Cyclization Reactions of Ethenetricarboxylates
路易斯酸促进乙烯三羧酸酯的环化反应
DOI:
--
发表时间:
2013
期刊:
影响因子:
--
作者:
[Yoshiteru Kawakami, Keita Tanaka, Marina Fukawa, Takayuki Sato, Yoshio Kabe, 下垣実央・藤田守文・杉村高志, S. Yamazaki]
通讯作者:
S. Yamazaki
反応性の高い共役付加受容体であるエテントリカルボン酸誘導体を用いる効率的合成反応
使用高度反应性共轭加合物受体乙烯三羧酸衍生物进行高效合成反应
DOI:
--
发表时间:
2014
期刊:
有機合成化学協会誌
影响因子:
--
作者:
[伊藤芳雄, 松村佳祐, 浅田佑紀, 鈴木彰, 山崎祥子]
通讯作者:
山崎祥子
Lewis Acid-Promoted Cyclization/Halogenation of Allenyl Ethenetricarboxylates and the Amides: Stereoselective Synthesis of Haloalkenyl Five-membered Heterocycles
路易斯酸促进烯基乙烯三羧酸酯和酰胺的环化/卤化:卤代烯基五元杂环的立体选择性合成
DOI:
10.1039/c4ob00233d
发表时间:
2014
期刊:
Org. Biomol. Chem.
影响因子:
--
作者:
[Fukushima, Y.; Yamazaki, S.; Ogawa, A.]
通讯作者:
A.
Lewis acid-promoted Cyclization Reactions of Allenyl Ethenetricarboxylates
路易斯酸促进烯丙基乙烯三羧酸酯的环化反应
DOI:
--
发表时间:
2012
期刊:
影响因子:
--
作者:
[S. Yamazaki, Y. Fukushim and A. Ogawa]
通讯作者:
Y. Fukushim and A. Ogawa
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