Photochemical formation and decomposition of 8-[β-arylethenyl]-2,2,6-trimethyl-7,9,10-trioxa-tricyclo[6.2.2.01,6]dodec-11-ene to novel 6-hydroxy-1,7,7-trimethyl-2-oxa-bicyclo[4.4.0]dec-4-en-3-one in the presence of oxygen

被引：4

作者：

Sharma, Vishal ^{[1
]}

Gupta, Vivek ^{[2
]}

Anthal, Sumati ^{[2
]}

Saxena, Ajit K. ^{[3
]}

Ishar, Mohan Paul S. ^{[1
]}

机构：

[1] Guru Nanak Dev Univ, Dept Pharmaceut Sci, Bioorgan & Photochem Lab, Amritsar 143005, Punjab, India

[2] Univ Jammu, Postgrad Dept Phys, Jammu 180006, India

[3] Indian Inst Integrat Med, Jammu 180006, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 42期

关键词：

(E; E)-Arylidene-beta-ionones; Photocycloaddition; Endoperoxides; Photodecomposition; CATALYZED CHEMILUMINESCENCE; ARTEMISININ DERIVATIVES; SINGLET OXYGEN; PHOTOOXYGENATION; 1,2,4-TRIOXANES; 1,2-DIOXETANES; ENDOPEROXIDE; CYTOTOXICITY;

D O I：

10.1016/j.tetlet.2012.08.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of (E,E)-arylidene-beta-ionones in the presence of oxygen leads to the formation of 8-[beta-arylethenyl]-2,2,6-trimethyl-7,9,10-trioxa-tricyclo[6.2.2.0(1,6)]dodec-11-enes (3). However, prolonged irradiation in the presence of oxygen leads to their conversion to 6-hydroxy-1,7,7-trimethyl-2-oxa-bicyclo [4.4.0]dec-4-en-3-one (4), apparently proceeding through addition of oxygen to the side chain pi-bond in 3. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5649 / 5651

页数：3

共 33 条

[1] PHOTOOXYGENATION OF TETRAMETHOXYBENZOBARRELENE - SYNTHESIS AND THERMAL-DECOMPOSITION OF BISDIOXETANE AND ENDOPEROXIDE [J].

ADAM, W ;

BALCI, M ;

CAKMAK, O ;

PETERS, K ;

SAHAMOLLER, CR ;

SCHULZ, M .

TETRAHEDRON, 1994, 50 (30) :9009-9024

[2]

[Anonymous], 2006, GUID TREATM MAL

[3]

[Anonymous], WHOCDSRBM200133

[4] A NOVEL DIOXETANE-HYDROPEROXIDE REARRANGEMENT - PHOTOOXYGENATION OF 3-TERT-BUTOXY (AND METHOXY)-6,7-BENZOBICYCLO[3,2,1]OCTA-2,6-DIENES [J].

BALCI, M ;

TASKESENLIGIL, Y ;

HARMANDAR, M .

TETRAHEDRON LETTERS, 1989, 30 (25) :3339-3342

[5] Versatility of the cyclo-oxymercuriation route to 1,2,4-trioxanes [J].

Bloodworth, AJ ;

Hagen, T ;

Johnson, KA ;

LeNoir, I ;

Moussy, C .

TETRAHEDRON LETTERS, 1997, 38 (04) :635-638

[6] PEROXY NATURAL-PRODUCTS [J].

CASTEEL, DA .

NATURAL PRODUCT REPORTS, 1992, 9 (04) :289-312

[7]

Casteel DA, 1999, NAT PROD REP, V16, P55

[8] Synthesis of α,β-unsaturated γ-lactones via photooxygenation of 2,3-dihydrofurans followed by ferrous ion-catalyzed gem-dehydration [J].

Chen, Yu-Zhe ;

Wu, Li-Zhu ;

Peng, Ming-Li ;

Zhang, Dong ;

Zhang, Li-Ping ;

Tung, Chen-Ho .

TETRAHEDRON, 2006, 62 (46) :10688-10693

[9]

DUSSAULT P, 1995, SYNLETT, P997

[10] Synthesis of 1,2-dioxanes, 1,2,4-trioxanes, and 1,2,4-trioxepanes via cyclizations of unsaturated hydroperoxyacetals [J].

Dussault, PH ;

Davies, DR .

TETRAHEDRON LETTERS, 1996, 37 (04) :463-466

← 1 2 3 4 →