The solar-chemical photo-Friedel-Crafts heteroacylation of 1,4-quinones

被引：35

作者：

Benites, Julio ^{[1
,2
]}

Rios, David ^{[1
,2
]}

Diaz, Pilar ^{[2
]}

Valderrama, Jaime A. ^{[1
,3
]}

机构：

[1] Univ Arturo Prat, Inst EtnoFarmacol IDE, Iquique, Chile

[2] Univ Arturo Prat, Dept Ciencias Quim & Farmaceut, Iquique, Chile

[3] Pontificia Univ Catolica Chile, Fac Quim, Santiago, Chile

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 05期

关键词：

Photo-Friedel-Crafts acylation; Heteroacylhydroquinones; Solar light; Photochemistry; Heterocycles; NATURALLY-OCCURRING QUINONES; AROMATIC-ALDEHYDES; MECHANISM; ACYLATION; ACCESS; 1,4-NAPHTHOQUINONES; PHOTOCHEMISTRY; HYDROQUINONES; ANGUCYCLINONE; ACETALDEHYDE;

D O I：

10.1016/j.tetlet.2010.11.149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photochemical reactions between 1,4-benzo- and 1,4-naphthoquinone and several heteroaromatic carbaldehydes were investigated under solar irradiation conditions. These reactions gave the corresponding heteroacylated hydroquinones in the range 71%-92% yield. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：609 / 611

页数：3

共 41 条

[1] Synthetic utility and mechanistic implications of the fries rearrangement of hydroquinone diesters in boron trifluoride complexes [J].

Boyer, JL ;

Krum, JE ;

Myers, MC ;

Fazal, AN ;

Wigal, CT .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4712-4714

[2] A SHORT SYNTHESIS OF DEOXYFRENOLICIN [J].

BRIMBLE, MA ;

LYNDS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05) :493-496

[3]

Bruce J. M., 1974, CHEM QUINOID COMPOUN, V1, P503

[4] LIGHT-INDUCED AND RELATED REACTIONS OF QUINONES .I. MECHANISM OF FORMATION OF ACETYLQUINOL FROM 1,4-BENZOQUINONE AND ACETALDEHYDE [J].

BRUCE, JM ;

CUTTS, E .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (04) :449-&

[5] LIGHT-INDUCED AND RELATED REACTIONS OF QUINONES .4. REACTION OF SOME P-QUINONES WITH ALIPHATIC AND AROMATIC ALDEHYDES [J].

BRUCE, JM ;

CREED, D ;

ELLIS, JN .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (16) :1486-&

[6] LIGHT-INDUCED AND RELATED REACTIONS OF QUINONES .5. SUBSTITUENT EFFECTS IN LIGHT-INDUCED REACTIONS BETWEEN PARA-QUINONES AND ALDEHYDES [J].

BRUCE, JM ;

DAWES, K .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (05) :645-&

[7] SYNTHESIS OF THE INSECTICIDAL 1'-ACETOXY-MAMMEINS AND SURANGIN-B [J].

CROMBIE, L ;

JONES, RCF ;

PALMER, CJ .

TETRAHEDRON LETTERS, 1985, 26 (24) :2933-2936

[8]

Dorofeenko G. N., 1971, KHIM GETEROTSIKL, V7, P1703

[9]

KLINGER H, 1891, BER DTSCH CHEM GES, V24, P1340, DOI DOI 10.1002/CBER.189102401234

[10]

KLINGER H, 1898, BER DTSCH CHEM GES, V31, P1214, DOI DOI 10.1002/CBER.189803101220

← 1 2 3 4 5 →