1,3-Dipolar cycloadditions of MeOPEG-bounded azides

被引：27

作者：

Molteni, G ^{[1
]}

Del Buttero, P ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy

来源：

TETRAHEDRON | 2005年 / 61卷 / 21期

关键词：

azides; 1,3-dipolar cycloadditions; azoles; polymer-supported synthesis;

D O I：

10.1016/j.tet.2005.03.049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloadditions of MeOPEG-supported azide 2 with a variety of dipolarophiles have been studied. 1-MeOPEG-supported 1,2,3-triazoles 4 and 5, 1,2,3,4-tetrazoles 12 and aziridine 14 were obtained in nearly quantitative yields. The removal of the MeOPEG moiety from the 1,2,3-triazole nucleus was achieved by acidic cleavage of the cycloadduct mixtures 4 and 5 giving 4- and 5-substituted-1,2,3-triazoles 6 and 7. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4983 / 4987

页数：5

共 42 条

[1] ALLIN SM, 1997, SYNTHESIS-STUTTGART, P1217
[2] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY
ALVAREZ, R
VELAZQUEZ, S
SANFELIX, A
AQUARO, S
DECLERCQ, E
PERNO, CF
KARLSSON, A
BALZARINI, J
CAMARASA, MJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) : 4185 - 4194
[3] REACTIONS OF UNSATURATED AZIDES .7. BASE-CATALYZED FORMATION OF ALLENYL AZIDES FROM PROPARGYL AZIDES - NEW SYNTHESES FOR 1,2,3-TRIAZOLES
BANERT, K
[J]. CHEMISCHE BERICHTE, 1989, 122 (10) : 1963 - 1967
[4] REACTIONS OF UNSATURATED AZIDES .6. SYNTHESIS OF 1,2,3-TRIAZOLES FROM PROPARGYL AZIDES BY REARRANGEMENT OF THE AZIDO GROUP - INDICATION OF SHORT-LIVED ALLENYL AZIDES AND TRIAZAFULVENES
BANERT, K
[J]. CHEMISCHE BERICHTE, 1989, 122 (05) : 911 - 918
[5] Improved procedure for the purification of PEG bound molecules by the use of trioctylamine
Benaglia, M
Cinquini, M
Cozzi, F
[J]. TETRAHEDRON LETTERS, 1999, 40 (10) : 2019 - 2020
[6] Applications of solid supported azide anion: a one-pot, two-step preparation of functionalized 1,2,3-triazoles
Blass, BE
Coburn, KR
Faulkner, AL
Seibel, WL
Srivastava, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (10) : 2153 - 2155
[7] BOURGOIS J, 1978, B SOC CHIM FR II-CH, P485
[8] Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides
Brockunier, LL
Parmee, ER
Ok, HO
Candelore, MR
Cascieri, MA
Colwell, LF
Deng, LP
Feeney, WP
Forrest, MJ
Hom, GJ
MacIntyre, DE
Tota, L
Wyvratt, MJ
Fisher, MH
Weber, AE
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (18) : 2111 - 2114
[9] An expedient route to the tetrazole analogues of α-amino acids
Demko, ZP
Sharpless, KB
[J]. ORGANIC LETTERS, 2002, 4 (15) : 2525 - 2527
[10] Demko ZP, 2002, ANGEW CHEM INT EDIT, V41, P2110, DOI 10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO

← 1 2 3 4 5 →