An efficient route to 1,8-dioxo-octahydroxanthenes and -decahydroacridines using a sulfated zirconia catalyst

被引：46

作者：

Kahandal, Sandeep S. ^{[1
]}

Burange, Anand S. ^{[2
]}

Kale, Sandip R. ^{[3
]}

Prinsen, Pepijn ^{[4
]}

Luque, Rafael ^{[4
]}

Jayaram, Radha V. ^{[5
]}

机构：

[1] BN Bandodkar Coll Sci, Dept Chem, Thana, India

[2] Wilson Coll Chowpatty, Dept Chem, Bombay, Maharashtra, India

[3] SIES, Coll Arts Sci & Commerce, Dept Chem, Bombay, Maharashtra, India

[4] Univ Cordoba, Dept Quim Organ, Ediftcio Marie Curie C-3,Ctra Nnal 4-A,Km 396, E-14014 Cordoba, Spain

[5] Inst Chem Technol, Dept Chem, Mumbai, Maharashtra, India

来源：

CATALYSIS COMMUNICATIONS | 2017年 / 97卷

关键词：

1,8-dioxo-octahydroxanthenes; 1,8-dioxo-decahydroacridines; Sulfated zirconia; Heterogeneous catalyst; POTENTIAL ANTITUMOR AGENTS; DERIVATIVES; ACID; CONDENSATION; DIACRIDINES; ALDEHYDES;

D O I：

10.1016/j.catcom.2017.03.017

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Sulfated zirconia results to be a very efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines without tedious work-up procedures. While 1,8-dioxo-octahydroxanthenes are prepared from aldehyde and 5,5-dimethyl-1,3-cyclohexenedione (dimedone), 1,8-dioxo-decahydroacridines are prepared from this reactant mixture with amines. This method provides a mild catalytic protocol for the synthesis of functionalized xanthene and acridine derivatives. The catalysts were characterized by XRD, FT-IR, TGA-DSC, SEM-EDAX and surface acidity and showed excellent re-usability up to 6 consecutive cycles.

引用

页码：138 / 145

页数：8

共 35 条

[1] Albert A., 1966, THE ACRIDINES, V2nd
[2] Palladium Supported on Fluorite Structured Redox CeZrO4-δ for Heterogeneous Suzuki Coupling in Water: A Green Protocol
Burange, Anand S.
Shukla, Rakesh
Tyagi, Avesh Kumar
Gopinath, Chinnakonda S.
[J]. CHEMISTRYSELECT, 2016, 1 (11): : 2673 - 2681
[3] Chavan A.A., 2016, CURR CATAL, V5, P129
[4] DIACRIDINES, BIFUNCTIONAL INTERCALATORS - CHEMISTRY AND ANTI-TUMOR ACTIVITY
CHEN, TK
FICO, R
CANELLAKIS, ES
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (09) : 868 - 874
[5] Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents
Chibale, K
Visser, M
van Schalkwyk, D
Smith, PJ
Saravanamuthu, A
Fairlamb, AH
[J]. TETRAHEDRON, 2003, 59 (13) : 2289 - 2296
[6] Structure-activity relationship for antineoplastic imidazoacridinones: Synthesis and antileukemic activity in vivo
Cholody, WM
Horowska, B
ParadziejLukowicz, J
Martelli, S
Konopa, J
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (05) : 1028 - 1032
[7] Diammonium hydrogen phosphate as a neutral and efficient catalyst for synthesis of 1,8-dioxo-octahydroxanthene derivatives in aqueous media
Darviche, Fatemeh
Balalaie, Saeed
Chadegani, Fatemeh
Salehi, Peyman
[J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) : 1059 - 1066
[8] Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines
Das, B
Thirupathi, P
Mahender, I
Reddy, VS
Rao, YK
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 247 (1-2) : 233 - 239
[9] POTENTIAL ANTITUMOR AGENTS .44. SYNTHESIS AND ANTITUMOR-ACTIVITY OF NEW CLASSES OF DIACRIDINES - IMPORTANCE OF LINKER CHAIN RIGIDITY FOR DNA-BINDING KINETICS AND BIOLOGICAL-ACTIVITY
DENNY, WA
ATWELL, GJ
BAGULEY, BC
WAKELIN, LPG
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (11) : 1568 - 1574
[10] Synthesis of two optically active calcium channel antagonists labelled with carbon-11 for in vivo cardiac PET imaging
Dolle, F
Hinnen, F
Valette, H
Fuseau, C
Duval, R
Peglion, JL
Crouzel, C
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (04) : 749 - 764

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