In(OTf)3-catalysed one-pot versatile pyrrole synthesis through domino annulation of α-oxoketene-N,S-acetals with nitroolefins

被引：20

作者：

Srivastava, Abhijeet ^{[1
]}

Shukla, Gaurav ^{[1
]}

Nagaraju, Anugula ^{[1
]}

Verma, Girijesh Kumar ^{[1
]}

Raghuvanshi, Keshav ^{[2
]}

Jones, Raymond C. F. ^{[3
]}

Singh, Maya Shankar ^{[1
]}

机构：

[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 05, Uttar Pradesh, India

[2] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany

[3] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 29期

关键词：

SOLVENT-FREE CONDITIONS; 3-COMPONENT REGIOSELECTIVE SYNTHESIS; HIGHLY SUBSTITUTED PYRROLES; DIAZO OXIME ETHERS; DUOCARMYCIN DERIVATIVES; FUNCTIONALIZED PYRROLES; ANTIOXIDANT ACTIVITY; EFFICIENT SYNTHESIS; ASSISTED SYNTHESIS; ANTITUMOR-ACTIVITY;

D O I：

10.1039/c4ob00781f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In(OTf)(3)-catalyzed robust and sustainable one-pot access to previously unknown and synthetically demanding polysubstituted pyrroles via [3 + 2] annulation of alpha-oxoketene-N,S-acetals with beta-nitrostyrenes has been achieved under solvent-free conditions. The merit of this domino Michael addition/cyclization sequence is highlighted by its operational simplicity, short reaction time (5-10 min), good to excellent yields, tolerance of a large variety of functional groups, and efficiency of producing two new (C-C and C-N) bonds and one highly functionalized pyrrole ring in a single operation, which make it an ideal alternative to existing methods.

引用

页码：5484 / 5491

页数：8

共 19 条

[1] In(OTf)3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones
Ghosh, R
Maiti, S
Chakraborty, A
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 217 (1-2) : 47 - 50
[2] A one-pot synthesis of bis(phenylimino)thiazolidines from ketene N,S-acetals and N,N′,-diphenyloxalimidoyl dichloride
Yavari, Issa
Zahedi, Nooshin
Baoosi, Leila
Skoulika, Stavroula
MOLECULAR DIVERSITY, 2018, 22 (01) : 11 - 19
[3] One-Pot Synthesis of Quinoxaline N-Oxides via Radical-Mediated Cyclization of Ketene N,S-Acetals
Kumar, Ganesh
Ray, Subhasish
Shukla, Gaurav
Singh, Maya Shankar
SYNTHESIS-STUTTGART, 2023, 55 (23): : 3981 - 3990
[4] La(OTf)3-catalysed one-pot synthesis of pyrazole tethered imidazo[1,2-a]azine derivatives and evaluation of their light emitting properties
Sharma, Shubham
Paul, Avijit Kumar
Singh, Virender
NEW JOURNAL OF CHEMISTRY, 2020, 44 (03) : 684 - 694
[5] One-pot synthesis of substituted isothiazol-3(2H)-ones:: Intramolecular annulation of α-carbamoyl ketene-S,S-acetals via PIFA-Mediated N-S bond formation
Huang, Jie
Lu, Yumei
Qiu, Baofu
Liang, Yongjiu
Li, Nan
Dong, Dewen
SYNTHESIS-STUTTGART, 2007, (18): : 2791 - 2796
[6] Cu(OTf)2/Et3N-promoted cyclocondensation of activated α-methylene alkenes and nitroolefins: a novel one-pot synthesis of polysubstituted benzenes
Su, Weike
Ding, Kai
Chen, Zhiwei
TETRAHEDRON LETTERS, 2009, 50 (06) : 636 - 639
[7] Cobalt Used as a Novel and Reusable Catalyst: A New and One-Pot Synthesis of Isatin-Derived N,S-Acetals Using Substituted Isatins and Thiols
da Silva, Caren D. G.
Katla, Ramesh
dos Santos, Beatriz F.
Tavares Junior, Jose M. C.
Albuquerque, Tabata B.
Kupfer, Vicente L.
Rinaldi, Andrelson W.
Domingues, Nelson L. C.
SYNTHESIS-STUTTGART, 2019, 51 (21): : 4014 - 4022
[8] Domino Reaction of Isatins with α-Oxoketene-N,S-acetals: An Efficient Synthesis of Pyrrolo[3,4-c]quinoline-1,3-diones and 2,3-Dihydro-1H-pyrrolo[3,4-c]quinolin-1-ones
Sharma, Anup Kumar
Jaiswal, Anjali
Chand, Shiv
Singh, Krishna Nand
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (11) : 2964 - 2968
[9] Chemoselective one-pot access to benzo[e]indole-4,5-diones and naphtho[2,1-b]thiophene-4,5-diones via copper-catalyzed oxidative [3+2] annulation of α-oxoketene N,S-acetals/β-ketothioamides with α-/β-naphthols
Yadav, Dhananjay
Shukla, Gaurav
Ansari, Monish A.
Srivastava, Abhijeet
Singh, Maya Shankar
TETRAHEDRON, 2018, 74 (40) : 5920 - 5931
[10] POLARIZED KETENE S,S-ACETALS AND S,N-ACETALS .66. CYCLOCONDENSATION OF ACYLKETENE S,N-ACETALS AND N,N-ACETALS WITH MALEIC-ANHYDRIDE AND MALEIMIDE - A FACILE ONE-STEP SYNTHESIS OF PYRANO[3,4-C]PYRROLE, PYRROLO[3,4-C]PYRIDINE AND CONDENSED PYRROLE DERIVATIVES
GUPTA, AK
ILA, H
JUNJAPPA, H
SYNTHESIS-STUTTGART, 1988, (04): : 284 - 286

← 1 2 →