Silica Sulfuric Acid (SSA) as a Highly Efficient Heterogeneous Catalyst for Persilylation of Purine and Pyrimidine Nucleobases and Other N-Heterocycles Using Hmds

被引：8

作者：

Rad, Mohammad Navid Soltani ^{[1
]}

Khalafi-Nezhad, Ali ^{[2
]}

Divar, Masoumeh ^{[2
]}

Behrouz, Somayeh ^{[2
]}

机构：

[1] Shiraz Univ Technol, Dept Chem, Fac Basic Sci, Shiraz 71555313, Iran

[2] Shiraz Univ, Dept Chem, Coll Sci, Shiraz, Iran

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2010年 / 185卷 / 09期

关键词：

HMDS; nucleobase; persilylation; silica sulfuric acid (SSA); CARBOACYCLIC NUCLEOSIDE SYNTHESIS; ONE-POT SYNTHESIS; HEXAMETHYLDISILAZANE HMDS; HYDROXYL-GROUPS; RAPID ENTRY; TRIMETHYLSILYL ETHERS; ALKYL PURINE; SOLVENT-FREE; ALCOHOLS; SILYLATION;

D O I：

10.1080/10426500903383952

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts.

引用

页码：1943 / 1954

页数：12

共 28 条

[1] Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies [J].

Amblard, F ;

Nolan, SP ;

Schinazi, RF ;

Agrofoglio, LA .

TETRAHEDRON, 2005, 61 (03) :537-544

[2] Efficient and practical protocol for silylation of hydroxyl groups using reusable lithium perchlorate dispersed in silica gel under neutral condition [J].

Azizi, N ;

Yousefi, R ;

Saidi, MR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (05) :817-820

[3] Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions [J].

Azizi, N ;

Saidi, MR .

ORGANOMETALLICS, 2004, 23 (06) :1457-1458

[4] CATALYSTS FOR SILYLATIONS WITH 1,1,1,3,3,3-HEXAMETHYLDISILAZANE [J].

BRUYNES, CA ;

JURRIENS, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3966-3969

[5] A novel class of phosphonate nucleosides. 9-[(1-phosphonomethoxycyclopropyl)methyl]guanine as a potent and selective anti-HBV agent [J].

Choi, JR ;

Cho, DG ;

Roh, KY ;

Hwang, JT ;

Ahn, S ;

Jang, HS ;

Cho, WY ;

Kim, KW ;

Cho, YG ;

Kim, J ;

Kim, YZ .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (11) :2864-2869

[6] CHEMISTRY AND ANTIVIRAL ACTIVITIES OF ACYCLONUCLEOSIDES [J].

CHU, CK ;

CUTLER, SJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) :289-319

[7] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[8]

COSSY J, 1978, TETRAHEDRON LETT, P6093

[9]

De Clercq E, 1993, ADV ANTIVIRAL DRUG D

[10]

Firouzabadi H, 2005, SYNTHESIS-STUTTGART, P595

← 1 2 3 →