Regioselectivity and diastereoselectivity of three-component reaction of α-amino acid, dialkyl acetylenedicarboxylates and 2-arylidene-1,3-indanediones

被引：10
|
作者：
Chen, Liang [1 ]
Sun, Jing [1 ]
Huang, Ying [1 ]
Zhang, Yu [1 ]
Yan, Chao-Guo [1 ]
机构：
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China
来源：
SCIENTIFIC REPORTS | 2017年 / 7卷
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; N-PHENACYLBENZOTHIAZOLIUM BROMIDES; AROMATIC-ALDEHYDES; CYCLOADDITION REACTION; 4-COMPONENT REACTIONS; EFFICIENT SYNTHESIS; DOMINO REACTIONS; FACILE SYNTHESIS; ARYLAMINES; CONSTRUCTION;
D O I：
10.1038/s41598-017-12361-z
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
The 1,3-dipolar cycloaddition of active azomethine ylide, which were generated in situ from addition reaction of alpha-amino acids with dialkyl acetylenedicarboxylates, with 2-arylidene-1,3-indanediones showed versatile regioselectivity and diastereoselectivity. The reaction of sarcosine and glycine afforded one kind of functionalized spiro[indene-2,3 '-pyrrolidines]. The other primary alpha-amino acids such as alanine, phenylalanine and leucine gave another kind of regioisomeric spiro[indene-2,3 '-pyrrolidines]. The cyclic alpha-amino acids resulted in the corresponding spiro[indene-2,2 '-pyrrolizines] and [indene-2,6 '-pyrrolo[1,2-c]thiazoles].
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页数：8
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