An Efficient Protocol for the Synthesis of Carboacyclic Nucleosides via Aza-Conjugate Addition Reaction

被引：0

作者：

Zolfigol, Mohammad Ali ^{[1
]}

Khazaei, Ardeshir ^{[1
]}

Moosavi-Zare, Ahmad Reza ^{[1
]}

Zare, Abdolkarim ^{[2
]}

Hasanijejad, Ali Reza ^{[3
]}

机构：

[1] Bu Ali Sina Univ, Fac Chem, Hamadan, Iran

[2] PNU, Dept Chem, Tehran, Iran

[3] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr, Iran

来源：

IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION | 2010年 / 29卷 / 04期

关键词：

Carboacyclic nucleoside; Aza-conjugate addition reaction; Pyrimidine nucleobase; alpha; beta-unsaturated ester; Microwave; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED ESTERS; PURINE NUCLEOBASES; HIGHLY EFFICIENT; PYRIMIDINE; CATALYST; GREEN; DERIVATIVES; SOLVENT;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to alpha,beta-unsaturated esters in the presence of catalytic amount of LiOH center dot H2O (1.2-4.8 mol%) under microwave irradiation is described. This method affords the title compounds in good to excellent yields and in short reaction times. [GRAPHICS]

引用

页码：67 / 73

页数：7

共 20 条

[1] Alkaline protease from Bacillus subtilis catalyzed Michael addition of pyrimidine derivatives to α,β-ethylenic compounds in organic media
Cai, Y
Sun, XF
Wang, N
Lin, XF
[J]. SYNTHESIS-STUTTGART, 2004, (05): : 671 - 674
[2] De Clercq Erik, 1993, V42, P1
[3] Neat reaction technology for the synthesis of 4-oxo-thiazolidines derived from 2-SH-benzothiazole and antimicrobial screening of some synthesized 4-thiazolidinones
Desai, K. G.
Raval, J. P.
Desai, K. R.
[J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2006, 3 (03) : 233 - 241
[4] Doerge R. F, 1982, WILSON GISVOLDS TXB
[5] Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds
Gimbert, Carolina
Moreno-Manas, Marcial
Perez, Elisabet
Vallribera, Adelina
[J]. TETRAHEDRON, 2007, 63 (34) : 8305 - 8310
[6] 6-(alkylamino)-9-alkylpurines. A new class of potential antipsychotic agents
Kelley, JL
Bullock, RM
Krochmal, MP
McLean, EW
Linn, JA
Durcan, MJ
Cooper, BR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (20) : 3207 - 3216
[7] Microwave-assisted Michael addition of some pyrimidine and purine nucleobases with α,β-unsaturated esters:: A rapid entry into carboacyclic nucleoside synthesis
Khalafi-Nezhad, A
Zarea, A
Rad, MNS
Mokhtari, B
Parhami, A
[J]. SYNTHESIS-STUTTGART, 2005, (03): : 419 - 424
[8] Synthesis of new acyclic nucleoside phosphonic acids by Michael addition
Lazrek, HB
Khaider, H
Rochdi, A
Barascut, JL
Imbach, JL
[J]. TETRAHEDRON LETTERS, 1996, 37 (27) : 4701 - 4704
[9] Synthesis of (Z) and (E) α-alkenyl phosphonic acid derivatives of purines and pyrimidines
Lazrek, HB
Rochdi, A
Khaider, H
Barascut, JL
Imbach, JL
Balzarini, J
Witvrouw, M
Pannecouque, C
De Clercq, E
[J]. TETRAHEDRON, 1998, 54 (15) : 3807 - 3816
[10] SOME MICHAEL-TYPE REACTIONS WITH ADENINE
LIRA, EP
HUFFMAN, CW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (07) : 2188 - &

← 1 2 →