Deep eutectic solvent: a simple, environmentally benign reaction media for regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles

被引：29

作者：

Kalmode, Hanuman P. ^{[1
]}

Vadagaonkar, Kamlesh S. ^{[1
]}

Murugan, Kaliyappan ^{[2
]}

Prakash, Sattey ^{[3
]}

Chaskar, Atul C. ^{[1
,3
]}

机构：

[1] Inst Chem Technol, Dept Dyestuff Technol, Bombay 400019, Maharashtra, India

[2] Natl Taiwan Univ, Taipei 10617, Taiwan

[3] Univ Mumbai, Natl Ctr Nanosci & Nanotechnol, Bombay 400098, Maharashtra, India

来源：

RSC ADVANCES | 2015年 / 5卷 / 44期

关键词：

ONE-POT SYNTHESIS; HIGHLY EFFICIENT SYNTHESIS; IONIC LIQUIDS; POLYSUBSTITUTED PYRROLES; FUNCTIONALIZED PYRROLES; 1,3-DICARBONYL COMPOUNDS; BIOLOGICAL EVALUATION; 3-COMPONENT SYNTHESIS; SUBSTITUTED PYRROLES; SOLID CATALYST;

D O I：

10.1039/c5ra03270a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Choline hydroxide has been successfully employed as an efficient base as well as reaction media for the synthesis of 2,3,4-trisubstituted 1H-pyrroles from methyl 2-isocyanoacetate and alpha,beta-unsaturated ketones. The choline hydroxide used is inexpensive, non-toxic, recyclable and environmentally friendly. Mild reaction conditions and an easy workup procedure are the striking features of this protocol. This transformation proceeds through the 1,4-conjugate addition of methyl 2-isocyanoacetate with alpha,beta-unsaturated ketones followed by intramolecular cyclization-oxidation reaction.

引用

页码：35166 / 35174

页数：9

共 50 条

[1] Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles:: A formal total synthesis of lukianol A
Liu, JH
Yang, QC
Mak, TCW
Wong, HNC
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3587 - 3595
[2] A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction
Kalmode, Hanuman P.
Vadagaonkar, Kamlesh S.
Murugan, Kaliyappan
Chaskar, Atul C.
NEW JOURNAL OF CHEMISTRY, 2015, 39 (06) : 4631 - 4639
[3] Highly Regioselective Synthesis of 2,3,4-Trisubstituted 1H-Pyrroles: A Formal Total Synthesis of Lukianol A (vol 65, pg 3587, 2000)
Liu, Jian-Hui
Yang, Qing-Chuan
Mak, Thomas C. W.
Wong, Henry N. C.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17): : 6906 - 6906
[4] Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide
Chen, Wenteng
Shao, Jiaan
Li, Zhi
Giulianotti, Marc A.
Yu, Yongping
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2012, 90 (02): : 214 - 221
[5] Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide
Yu, Y. (yyu@zju.edu.cn), 1600, Canadian Science Publishing (90):
[6] A REGIOCONTROLLED SYNTHESIS OF 2,3,4-TRISUBSTITUTED PYRROLES FROM DISUBSTITUTED CHLOROPROPENIMINIUM SALTS
PETRICH, SA
GUPTON, JT
BRUCE, MA
VU, P
SWINNEY, CP
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 73 - CHED
[7] Dearomatization Strategy for the Synthesis of Arylated 2H-Pyrroles and 2,3,5-Trisubstituted 1H-Pyrroles
Polak, Peter
Tobrman, Tomas
ORGANIC LETTERS, 2017, 19 (17) : 4608 - 4611
[8] The utilization of Rink amide resin in the solid phase synthesis of 2,3,4-trisubstituted pyrroles
Sellitto, Eric
McCranor, Bryan
Burnham, Bruce S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[9] New efficient, flexible and regioselective synthesis of 2,4-di- and 2,3,4-trialkylated and arylated 1H-pyrroles
Enders, D
Maassen, R
Han, SH
LIEBIGS ANNALEN, 1996, (10): : 1565 - 1574
[10] Regioselective Synthesis of Highly Functionalized 2H-Pyrroles via Dearomative Chlorination of 1H-Pyrroles
Shambalova, Victoria E.
Larkovich, Roman V.
Aldoshin, Alexander S.
Lyssenko, Konstantin A.
Nechaev, Mikhail S.
Nenajdenko, Valentine G.
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (16): : 11394 - 11407

← 1 2 3 4 5 →