CuBr-mediated synthesis of 1,4-naphthoquinones via ring expansion of 2-aryl-1,3-indandiones

被引：4

作者：

Zhang, Xu ^{[1
]}

Wang, Di ^{[1
]}

Chang, Mengfan ^{[1
]}

Wang, Wanya ^{[1
]}

Shen, Zhi ^{[1
]}

Xu, Xuefeng ^{[1
]}

机构：

[1] Nanyang Normal Univ, Coll Chem & Pharmaceut Engn, Nanyang 473061, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 82期

关键词：

C-H BONDS; ORGANOTRANSITION-METAL SYNTHESIS; CHEMOSELECTIVE ACTIVATION; CARBENE COMPLEXES; BENZANNULATION; JUGLONE; KETONES; HOMOLOGATION; DERIVATIVES; PLUMBAGIN;

D O I：

10.1039/d3cc03753c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A CuBr-mediated direct insertion of alkenes into unstrained ring 2-aryl-1,3-indandiones is reported, which provides a one-carbon ring expansion strategy for the synthesis of 1,4-naphthoquinones. Entirely differing from the existing reports, the alkenes herein behave as C1 units to participate in annulation reactions. This transformation provides a facile route to access a class of highly functionalized 1,4-naphthoquinones with good yields, good functional-group tolerance and high atom-economy. Further research on the application of this reaction is currently underway in our laboratory.

引用

页码：12326 / 12329

页数：4

共 50 条

[21] SYNTHESIS AND CONVERSIONS OF POLYFLUORINATED 1,3-INDANDIONES .2.
OSADCHII, SA
BARKHASH, VA
ZHURNAL ORGANICHESKOI KHIMII, 1970, 6 (09): : 1815 - &
[22] PHTHALIDES AND 1,3-INDANDIONES .43. PREPARATION OF 2-(1-NAPHTHYL)-1,3-INDANDIONES AND 2-(2-NAPHTHYL)-1,3-INDANDIONES SUBSTITUTED IN POSITION 5 OF INDANDIONE RING AND IN POSITION 4(1) OF NAPHTHALENE RING
HRNCIAROVA, M
HRNCIAR, P
CHEMICKE ZVESTI, 1971, 25 (03): : 215 - +
[23] Asymmetric synthesis of multicyclic spiro-1,3-indandiones via a cascade Michael/Michael reaction of curcumins and 2-arylidene-1,3-indandiones
Luo, Nian-hua
Sun, Xiang
Wei, Wen-tao
Zhang, Xue-jing
Yan, Ming
TETRAHEDRON-ASYMMETRY, 2013, 24 (07) : 402 - 408
[24] Synthesis of Mixed Aryl 2,3-Diarylsulphanyl-1,4-naphthoquinones
Singh, W. Marjit
Baruah, Jubaraj B.
SYNTHETIC COMMUNICATIONS, 2009, 39 (08) : 1433 - 1442
[25] INHIBITION OF COMPLEMENT BY A SERIES OF SUBSTITUTED 2-ARYL-1,3-INDANDIONES - INTERACTION WITH THE 5TH COMPONENT OF COMPLEMENT
ASGHAR, SS
SIDDIQUI, AH
VANDERGOOT, H
TIMMERMAN, H
MOLECULAR IMMUNOLOGY, 1986, 23 (05) : 459 - 465
[26] METABOLISM OF 2-ARYL-1,3-INDANDIONES .1. UV-VIS-SPECTRO-PHOTOMETRIC ASSAY OF 2-PHENYL-1,3-INDANDIONE
DEVRIES, J
VERBOOM, CN
VANDERHEIJDEN, PJCM
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1976, 11 (04) : 317 - 321
[27] PHARMACOCHEMISTRY OF 2-DIARYLMETHYL-1,3-INDANDIONES .1. SYNTHESIS
WINTER, MLD
NAUTA, WT
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1977, 12 (02) : 125 - 130
[28] SYNTHESIS OF 2-PIPERAZINODERIVATIVES OF 1,4-NAPHTHOQUINONES
BEREZHNAYA, VN
SHISHKINA, RP
FOKIN, EP
IZVESTIYA SIBIRSKOGO OTDELENIYA AKADEMII NAUK SSSR SERIYA KHIMICHESKIKH NAUK, 1987, (02): : 101 - 104
[29] FURTHER STUDIES CONCERNING EFFECTS OF 2-ARYL-1,3-INDANDIONES ON OXIDATIVE-PHOSPHORYLATION IN RAT-LIVER MITOCHONDRIA
VANDENBERG, G
WOLTERS, D
NAUTA, WT
BIOCHEMICAL PHARMACOLOGY, 1975, 24 (23) : 2149 - 2152
[30] 2-ARYL-2-(IODOMETHYL)-1,3-INDANDIONES AND THEIR REACTION WITH TETRIARY HETEROCYCLIC AMINES
VALTER, RE
VANAG, GY
JOURNAL OF GENERAL CHEMISTRY USSR, 1964, 34 (03): : 804 - &

← 1 2 3 4 5 →