Facile three-component reactions for the synthesis of N-unsubstituted 1H-pyrrol-3(2H)-ones and base induced divergent N-H and C-C bond derivatizations

被引：4

作者：

Cao, Jia-xuan ^{[1
]}

Hua, Wei-jie ^{[1
]}

Jiang, Jun-cen ^{[1
]}

Chen, Min ^{[1
]}

Sha, Qiang ^{[1
]}

机构：

[1] Nanjing Agr Univ, Coll Sci, Dept Chem, Jiangsu Key Lab Pesticide Sci, 1 Weigang Rd, Nanjing 210095, Peoples R China

来源：

TETRAHEDRON | 2022年 / 125卷

关键词：

Heterocycles; Multicomponent reactions; Cascade reactions; 2; 3-Diketoesters; Rearrangement reactions; METAL-FREE SYNTHESIS; CYCLIZATION; CHEMISTRY; DERIVATIVES; CASCADE; PYRROLIN-4-ONES; ALKALOIDS; MIGRATION; EFFICIENT; DESIGN;

D O I：

10.1016/j.tet.2022.133038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we present a facile three-component reaction of 2,3-diketoesters, ammonium acetate and ke-tones that yielded a variety of N-unsubstituted 1H-pyrrol-3(2H)-ones in moderate to good yields. Sub-sequently, base-induced divergent N-H and C-C bond derivatizations of N-unsubstituted 1H-pyrrol-3(2H)-ones were revealed. By using NaH as the base, N-alkylation, acylation and sulfonylation occur smoothly. When NaOH is used, C-C(1/4O) cleavage occurs and further Michael addition reaction happens, resulting in the installation of an alkyl chain at the 2-position of the 1H-pyrrol-3(2H)-one skeleton.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：6

共 50 条

[41] Domino reactions in the synthesis of tetrahydropyrimidin-2(1H)-ones(thiones) annelated at the N(1)-C(6) bond (Review)
Fisyuk, A. S.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (04) : 548 - 565
[42] Domino reactions in the synthesis of tetrahydropyrimidin-2(1H)-ones(thiones) annelated at the N(1)–C(6) bond (Review)
A. S. Fisyuk
Chemistry of Heterocyclic Compounds, 2012, 48 : 548 - 565
[43] N-H Insertion Reactions Catalyzed by a Dirhodium Metal-Organic Cage: A Facile and Recyclable Approach for C-N Bond Formation
Kang, Jian
Chen, Lianfen
Cui, Hao
Zhang, Li
Su, Cheng-Yong
CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (06) : 964 - 968
[44] Synthesis of 3-Methyleneisoindolin-1-ones via Rhodium(III)-Catalyzed C-H/N-H Activation and Annulation of N-Methoxybenzamides with Potassium Vinyltrifluoroborate
Kumar, Vikash
Gandeepan, Parthasarathy
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (22)
[45] Bond-forming reactions of N22+ with C2H4, C2H6, C3H4 and C3H6
Fletcher, James D.
Parkes, Michael A.
Price, Stephen D.
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2015, 377 : 101 - 108
[46] AZEPINONES .5. BASE-INDUCED RING CONTRACTION OF N-SUBSTITUTED 1H-AZEPIN-3(2H)-ONES
MCNAB, H
MONAHAN, LC
JOURNAL OF CHEMICAL RESEARCH-S, 1990, (10): : 336 - 337
[47] Palladium N-heterocyclic carbene catalyzed expected and unexpected C-C and C-N functionalization reactions of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones
Purohit, Vishal B.
Karad, Sharad C.
Patel, Kirit H.
Raval, Dipak K.
RSC ADVANCES, 2016, 6 (112): : 111139 - 111143
[48] An air-stable [Cu(NHC)(OR)] (R = C(H)(CF3)2) complex for C-H, N-H and S-H bond activation
Ostrowska, Sylwia
Arnaut, Pierre
Liptrot, David J.
Cazin, Catherine S. J.
Nolan, Steven P.
CHEMICAL COMMUNICATIONS, 2023, 59 (59) : 9126 - 9129
[49] Ru(II)-Catalyzed annulation of benzamidines and alkynes by C-H/N-H activation: a facile synthesis of 1-aminoisoquinolines
Kaishap, P. P.
Duarah, G.
Chetia, D.
Gogoi, S.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (16) : 3491 - 3498
[50] Hydrogen atom transfer reactions of C2-, C4-, and C6-:: Bond dissociation energies of linear H-C2n- and H-C2n (n=1, 2, 3)
Shi, Yang
Ervin, Kent A.
JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (06): : 1261 - 1267

← 1 2 3 4 5 →