Highly Regioselective and Diastereoselective, One-Pot, Four-Component Synthesis of Novel Spiroindenoquinoxalineindolizidine Derivatives

被引：4

作者：

Moemeni, Mehdi ^{[1
]}

Arvinnezhad, Hamid ^{[1
]}

Samadi, Saadi ^{[1
]}

Salahi, Farbod ^{[1
]}

Jadidi, Khosrow ^{[1
]}

Notash, Behrouz ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Fac Sci, Dept Chem, GC, Tehran, Iran

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2015年 / 52卷 / 03期

关键词：

1,3-DIPOLAR CYCLOADDITION REACTION; QUINOLIZIDINE ALKALOIDS; IONIC LIQUID; INDOLIZIDINE; PYRROLIZIDINES;

D O I：

10.1002/jhet.2121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, four-component procedure for the synthesis of novel spiroindenoquinoxalineindolizidines with high regioselectivity and diastereoselectivity from the 1,3-dipolar cycloaddition of azomethine ylides, generated from indenoquinoxalines and pipecolinic acid, and chalcones is described. The reaction occurs under reflux of ethanol as a green solvent and in the absence of any catalyst. The cycloadducts are obtained purely without future purification. The regiochemistry and stereochemistry of resultant cycloadducts have been determined by several 2D-NMR spectroscopic techniques and X-ray single crystal diffraction.

引用

页码：944 / 948

页数：5

共 50 条

[21] One-pot, three-component, green procedure for efficient synthesis of allomaltol derivatives
Yu-Ling Li
Kai Wang
Bo Zhao
Qiu-Shi Jiang
Bai-Xiang Du
Cai-Fa Chen
Research on Chemical Intermediates, 2015, 41 : 5149 - 5158
[22] An expedient sequential one-pot four component synthesis of novel steroidal spiro-pyrrolidine heterocycles in ionic liquid
Gavaskar, D.
Babu, A. R. Suresh
Raghunathan, R.
Dharani, M.
Balasubramanian, S.
STEROIDS, 2016, 109 : 1 - 6
[23] One-pot synthesis of tetrahydrochromene derivatives catalyzed by lipase
Xu, Jiang-Cheng
Li, Wan-Mei
Zheng, Hui
Lai, Yi-Feng
Zhang, Peng-Fei
TETRAHEDRON, 2011, 67 (49) : 9582 - 9587
[24] A Cheap Amino Alcohol Catalyzed One-Pot, Tri-Component Synthesis of Tetrahydrochromene Derivatives
Song, Shaojun
Shan, Zixing
Jin, Yong
LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (01) : 64 - 68
[25] Efficient One-Pot Three-Component Synthesis of Fused Pyridine Derivatives in Ionic Liquid
Huang, Zhibin
Hu, Yu
Zhou, Yao
Shi, Daqing
ACS COMBINATORIAL SCIENCE, 2011, 13 (01) : 45 - 49
[26] Synthesis of benzo[g]indeno[2,1-b]quinoline derivatives via four-component and one-pot synthesis in presence of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate
Khaligh, Nader Ghaffari
CHINESE JOURNAL OF CATALYSIS, 2014, 35 (11) : 1858 - 1863
[27] One-pot, four-component synthesis of novel biologically important indeno[2,3-b]quinoxaline]-3-carbonitriles in fluoro-alcohols under ultrasound irradiation
Heravi, Mohammad Reza Poor
Norouzy, Fatemeh
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (07) : 4265 - 4282
[28] Application of Cu (II)-Guanine Complexes Anchored on SBA-15 and MCM-41 as Efficient Nanocatalysts for One-Pot, Four-Component Domino Synthesis of Phenazine Derivatives and Investigation of Their Antimicrobial Behavior
Nikoorazm, Mohsen
Khanmoradi, Maryam
CATALYSIS LETTERS, 2020, 150 (10) : 2823 - 2840
[29] Ugi Four-Component Assembly Process: An Efficient Approach for One-Pot Multifunctionalization of Nanographene Oxide in Water and Its Application in Lipase Immobilization
Rezaei, Aram
Akhavan, Omid
Hashemi, Ehsan
Shamsara, Mehdi
CHEMISTRY OF MATERIALS, 2016, 28 (09) : 3004 - 3016
[30] One-pot, three-component Synthesis of pyrrolo[2,3-d]pyrimidine Derivatives
Javahershenas, Ramin
Khalafy, Jabbar
JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2018, 62 (01)

← 1 2 3 4 5 →