Synthesis of 2,3,5-trisubstituted 1H-pyrroles via formal [3+2] cycloaddition of 1-arylpropynes and nitriles and their antiproliferative activities

被引：0

作者：

He, Dandan ^{[1
,2
,3
]}

Li, Ling ^{[1
,2
,3
]}

Wen, Xiong ^{[1
,2
,3
]}

Yin, Luxiang ^{[1
,2
,3
]}

Li, Jue ^{[1
,2
,3
]}

Wu, Sha ^{[1
,2
,3
]}

Li, Huili ^{[1
,2
,3
]}

Jiang, Fei ^{[1
,2
,3
]}

Shen, Xiangchun ^{[1
,2
,3
]}

机构：

[1] Guizhou Med Univ, Minist Educ, State Key Lab Funct & Applicat Med Plants, Key Lab Endem & Ethn Dis, 6 Ankang Ave & Guian New Dist, Guiyang 561113, Guizhou, Peoples R China

[2] Guizhou Med Univ, High Efficacy Applicat Nat Med Resources Engn Ctr, Key Lab Optimal Utilizat Nat Med Resources, 6 Ankang Ave & Guian New Dist, Guiyang 561113, Guizhou, Peoples R China

[3] Guizhou Med Univ, High Educ Key Lab Guizhou Prov Nat Med Pharmacol, 6 Ankang Ave & Guian New Dist, Guiyang 561113, Guizhou, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2025年 / 12卷 / 04期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; H BOND ADDITION; TETRASUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; DERIVATIVES; 2H-AZIRINES; ACCESS;

D O I：

10.1039/d4qo01999g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward approach for the assembly of 2,3,5-trisubstituted 1H-pyrroles via a base-mediated [3 + 2] cycloaddition of 1-arylpropynes with nitriles has been reported through alkali metal salt-promoted C(sp3)-H functionalization. This reaction features a transition metal-free catalyst, facile starting materials and a wide substrate scope. Moreover, the biological evaluation revealed that these pyrrole products exhibit antiproliferative activities against MDA-MB-231, SGC-7901, and HCT-116 cells, which provides potential applications in pharmaceutical chemistry.

引用

页码：1150 / 1155

页数：6

共 50 条

[41] SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS BY THE ACID-CATALYZED DECOMPOSITION OF 1,2-DIOXAN-3-OLS
QIAN, CY
HIROSE, J
NISHINO, H
KUROSAWA, K
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (05) : 1219 - 1227
[42] 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
[43] Mechanochemical Synthesis of 1,2,4-Triazoles via a [3+2] Cycloaddition of Azinium-N-Imines and Nitriles
Zhu, Baofu
Li, Wen
Chen, Haixin
Wu, Minjian
Hu, Jijing
Cao, Hua
Liu, Xiang
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (17) : 2911 - 2915
[44] Regioselective Synthesis of Functionalized Pyrroles via Gold(I)-Catalyzed [3+2] Cycloaddition of Stabilized Vinyl Diazo Derivatives and Nitriles
Lonzi, Giacomo
Lopez, Luis A.
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (10) : 1948 - 1954
[45] Synthesis of 3,4,5-trisubstituted isoxazoles via sequential [3+2] cycloaddition/silicon-based cross-coupling reactions
Denmark, SE
Kallemeyn, JM
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07): : 2839 - 2842
[46] Synthesis of Pyrroles in Supercritical Carbon Dioxide: Formal [3+2] Cycloaddition of 2-Benzoyl-Aziridines and Allenoates
Cardoso, Ana L.
Nunes, Rui M. D.
Arnaut, Luis G.
Pinho e Melo, Teresa M. V. D.
SYNTHESIS-STUTTGART, 2011, (21): : 3516 - 3522
[47] Deep eutectic solvent: a simple, environmentally benign reaction media for regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles
Kalmode, Hanuman P.
Vadagaonkar, Kamlesh S.
Murugan, Kaliyappan
Prakash, Sattey
Chaskar, Atul C.
RSC ADVANCES, 2015, 5 (44) : 35166 - 35174
[48] Studies on the Formal [3+2] Cycloaddition of Aziridines with Alkenes for the Synthesis of 1-Azaspiroalkanes
Martinand-Lurin, Elodie
Gruber, Raymond
Retailleau, Pascal
Fleurat-Lessard, Paul
Dauban, Philippe
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1414 - 1426
[49] Alkyne [3+2] Cycloadditions of Iodosydnones Toward Functionalized 1,3,5-Trisubstituted Pyrazoles
Browne, Duncan L.
Taylor, John B.
Plant, Andrew
Harrity, Joseph P. A.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03): : 984 - 987
[50] Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3+2] Cycloaddition
Cholewczynski, Anna E.
Williams, Peyton C.
Pierce, Joshua G.
ORGANIC LETTERS, 2020, 22 (02) : 714 - 717

← 1 2 3 4 5 →