One-pot synthesis of 5,6-disubstituted 3H-pyrrolizines organocatalyzed by piperidinium acetate

被引：13

作者：

Li, Yujiao ^{[1
,2
]}

Yan, Jiaying ^{[1
,2
]}

Cheng, Kai ^{[1
,2
]}

Kong, Shuai ^{[1
,2
]}

Zheng, Kaibo ^{[1
,2
]}

Wang, Long ^{[1
,2
]}

Zhang, Nuonuo ^{[1
,2
]}

机构：

[1] China Three Gorges Univ, Coll Mat & Chem Engn, Yichang 443002, Hubei, Peoples R China

[2] China Three Gorges Univ, Key Lab Inorgan Nonmetall Crystalline & Energy Co, Yichang 443002, Hubei, Peoples R China

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2017年 / 43卷 / 10期

基金：

中国国家自然科学基金;

关键词：

3H-Pyrrolizine; Organocatalyst; Piperidinium acetate; One-pot; DFT calculation; PYRROLIZINE DERIVATIVES; EFFICIENT SYNTHESIS; INHIBITORS; DESIGN;

D O I：

10.1007/s11164-017-2929-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The organocatalyst, piperidinium acetate formed in situ, was utilized as an efficient catalyst for one-pot synthesis of 5,6-disubstituted 3H-pyrrolizines with halogen (Cl, Br), methoxy and ethyl ester groups. Absorption and emission spectra properties were also compared in dichloromethane, toluene, methanol, and DMSO. Electronic spectra were altered slightly by these substituents, which can be well explained by TD-DFT calculations. And the selected four orbital energies indicated that electrons transited smoothly from the pyrrolizine ring to the indole unit.

引用

页码：5337 / 5344

页数：8

共 50 条

[41] One-pot synthesis of nucleoside 5′-triphosphates from nucleoside 5′-H-phosphonates
Sun, Qi
Edathil, Jocelyn P.
Wu, Runzhi
Smidansky, Eric D.
Cameron, Craig E.
Peterson, Blake R.
ORGANIC LETTERS, 2008, 10 (09) : 1703 - 1706
[42] One-Pot Microwave-Assisted Synthesis of 3,4-Disubstituted 2-Quinolinones
Bui, Chinh T.
SYNTHETIC COMMUNICATIONS, 2014, 44 (08) : 1122 - 1127
[43] Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles
Mohamady, Samy
Kralt, Braden
Samwel, Shery K.
Taylor, Scott D.
ACS OMEGA, 2018, 3 (11): : 15566 - 15574
[44] Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
Hue Thi Buu Bui
Kiep Minh Do
Huy Tran Duc Nguyen
Hieu Van Mai
Thanh La Duc Danh
De Quang Tran
Morita, Hiroyuki
TETRAHEDRON, 2021, 98
[45] One-pot synthesis of 5-alkylthio-3H-1,2-dithiole-3-thiones:: Advantages and scopes
Aimar, ML
de Rossi, RH
SYNTHESIS-STUTTGART, 2000, (12): : 1749 - 1755
[46] CONDENSATION OF DIMETHYL-3-METHYLGLUTACONATE WITH ALDEHYDES - A ONE-POT SYNTHESIS OF FUNCTIONALIZED 5,6-DIHYDRO-(2H)-PYRAN-2-ONES
DUSSERT, AS
AUDIN, P
PARIS, J
SYNLETT, 1993, (07) : 507 - 508
[47] SYNTHESIS AND ANTI-TUMOR EVALUATION OF SELECTED 5,6-DISUBSTITUTED 1(2)H-INDAZOLE-4,7-DIONES
CONWAY, GA
LOEFFLER, LJ
HALL, IH
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) : 876 - 884
[48] Three-Component, One-Pot Sequential Synthesis of 1,3-Disubstituted 5-Arylhydantoins
Olimpieri, Francesca
Volonterio, Alessandro
Zanda, Matteo
SYNLETT, 2008, (19) : 3016 - 3020
[49] One-pot synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones
Zhang, Ying-Qun
Ma, Jing-Jun
Wang, Chun
Li, Jing-Ci
Zhang, Dong-Nuan
Zang, Xiao-Huan
Li, Jie
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (01) : 141 - 144
[50] One-pot tandem synthesis of fluorescent 5-naphthy1-3(2H)-furanones
Mal'kina, Anastasiya G.
Volostnykh, Ol'ga G.
Petrushenko, Konstantin B.
Shemyakina, Olesya A.
Nosyreva, Valentina V.
Ushakov, Igor' A.
Trofimov, Boris A.
TETRAHEDRON, 2013, 69 (18) : 3714 - 3720

← 1 2 3 4 5 →