Reactions of 2-[Lithio(trimethylsilyl)methyl]-2H-tetrazoles: Synthesis of 2-[1-(Trimethylsilyl) alkyl]-2H-tetrazoles and (2H-Tetrazol-2-yl) acetates

被引：2

作者：

Umemoto, Hideaki ^{[1
]}

Onaka, Takuya ^{[1
]}

Miki, Yasuyoshi ^{[2
]}

Nakamura, Akira ^{[2
]}

Maegawa, Tomohiro ^{[2
]}

机构：

[1] Fujimoto Chem Co Ltd, Amagasaki, Hyogo 6600806, Japan

[2] Kinki Univ, Sch Pharmaceut Sci, Higashi Osaka 5778502, Japan

来源：

SYNLETT | 2015年 / 26卷 / 02期

关键词：

tetrazoles; synthetic methods; lithiation; synthons; 5-SUBSTITUTED TETRAZOLES; CANDESARTAN; ALKYLATION; LOSARTAN; ACIDS;

D O I：

10.1055/s-0034-1378933

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-[(trimethylsilyl) methyl]-2H-tetrazoles with various alkyl halides and carbonates using n-butyllithium or lithium diisopropylamide (LDA) gave 2-[1-(trimethylsilyl) alkyl]-2H-tetrazoles and (2H-tetrazol-2-yl) acetates as useful synthons of modified tetrazoles.

引用

页码：205 / 208

页数：4

共 34 条

[1] Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan
Alonen, Anna
Jansson, Johanna
Kallonen, Sirkku
Kiriazis, Alexandros
Aitio, Olli
Finel, Moshe
Kostiainen, Risto
[J]. BIOORGANIC CHEMISTRY, 2008, 36 (1-3) : 148 - 155
[2] The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan
Alonen, Anna
Finel, Moshe
Kostiainen, Risto
[J]. BIOCHEMICAL PHARMACOLOGY, 2008, 76 (06) : 763 - 772
[3] Arora J., 2005, Patent, Patent No. [2005080386, WO 2005, 080, 386]
[4] Arora J., 2005, CHEM ABSTR, V143
[5] Arzel E., 2009, [No title captured], Patent No. [WO 2009 051 556, 2009151556]
[6] Arzel E., 2009, CHEM ABSTR, V150
[7] 1,3-dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles
Aureggi, Valentina
Sedelmeier, Gottfried
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) : 8440 - 8444
[8] Carboxylic acid bioisosteres of gamma-linked dipeptide analogues of the folate-based thymidylate synthase (TS) inhibitor, 2-desamino-2-methyl-N-10-propargyl-5,8-dideazafolic acid (ICI 198583)
Bavetsias, V
Jackman, AL
Kimbell, R
Boyle, FT
Bisset, GMF
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (06) : 631 - 636
[9] Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II, V4
[10] Chul L.S., 2010, CHEM ABSTR, V154, P86383

← 1 2 3 4 →