Metal-free cascade reactions of aziridines with arylalkynes and aryldiazoniums: facile access to arylazopyrrolines

被引：10

作者：

Rong, Jing ^{[1
]}

Jiang, Hao ^{[1
]}

Wang, Sijing ^{[1
]}

Su, Zhenni ^{[1
]}

Wang, Huiyan ^{[1
]}

Tao, Chuanzhou ^{[1
]}

机构：

[1] Jiangsu Ocean Univ, Sch Chem Engn, Lianyungang 222005, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 16期

基金：

中国国家自然科学基金;

关键词：

MUTUAL AZO PRODRUGS; 2,3-DIHYDROPYRROLES; DESIGN; AGENTS; ACID; DERIVATIVES; CYCLIZATION; INHIBITORS; ASSEMBLIES; COMPLEXES;

D O I：

10.1039/d0ob00346h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and facile approach to synthesize arylazopyrroline scaffolds via metal-free cascade reactions of aziridines with arylalkynes and aryldiazoniums has been developed, providing access to a variety of 4-arylazo-2-pyrrolines in a highly concise fashion. This efficient process, which can be performed at the gram scale, enjoys operational simplicity and mild and metal-free conditions.

引用

页码：3149 / 3157

页数：9

共 49 条

[11] Facile construction of highly functionalized 2-pyrrolines via FeCl3-catalyzed reaction of aziridines with arylalkynes
Fan, Jinmin
Gao, Linfeng
Wang, Zhiyong
[J]. CHEMICAL COMMUNICATIONS, 2009, (33) : 5021 - 5023
[12] Synthesis and Intramolecular Azo Coupling of 4-Diazopyrrole-2-carboxylates: Selective Approach to Benzo and Hetero [c]-Fused 6H-Pyrrolo[3,4-c]pyridazine-5-carboxylates
Galenko, Ekaterina E.
Galenko, Alexey V.
Khlebnikov, Alexander F.
Novikov, Mikhail S.
Shakirova, Julia R.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (18) : 8495 - 8507
[13] An enantioselective formal synthesis of the proteasome inhibitor (+)-lactacystin
Green, MP
Prodger, JC
Hayes, CJ
[J]. TETRAHEDRON LETTERS, 2002, 43 (37) : 6609 - 6611
[14] Bromoallenes as allyl dication equivalents in the absence of palladium(0): Synthesis of bicyclic sulfamides by tandem cyclization of bromoallenes
Hamaguchi, H
Kosaka, S
Ohno, H
Tanaka, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) : 1513 - 1517
[15] Azobenzenes-synthesis and carbohydrate applications
Hamon, Florian
Djedaini-Pilard, Florence
Barbot, Francis
Len, Christophe
[J]. TETRAHEDRON, 2009, 65 (49) : 10105 - 10123
[16] Dendritic azo compounds as a new type amorphous molecular material with quick photoinduced surface-relief-grating formation ability
He, Yaning
Gu, Xinyu
Guo, Miaocai
Wang, Xiaogong
[J]. OPTICAL MATERIALS, 2008, 31 (01) : 18 - 27
[17] Hunger K., 2007, IND DYES CHEM PROPER
[18] The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups:: syntheses of ring-fluorinated dihydroheteroaromatics
Ichikawa, J
Fujiwara, M
Wada, Y
Okauchi, T
Minami, T
[J]. CHEMICAL COMMUNICATIONS, 2000, (19) : 1887 - 1888
[19] Synthesis of Mutual Azo Prodrugs of Anti-inflammatory Agents and Peptides Facilitated by α-Aminoisobutyric Acid
Kennedy, David A.
Vembu, Nagarajan
Fronczek, Frank R.
Devocelle, Marc
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) : 9641 - 9647
[20] Hydrazonoyl Chlorides as Precursors for Synthesis of Novel Bis-Pyrrole Derivatives
Kheder, Nabila Abdelshafy
[J]. MOLECULES, 2016, 21 (03):

← 1 2 3 4 5 →