5-Aminofuro[3,2-c]pyridinium Tosylates and Substituted Furo[3,2-c]pyridine N-Oxides: Synthesis and Reactions

[img]PDF - Authorized users only
Language: English
90Kb
Title:5-Aminofuro[3,2-c]pyridinium Tosylates and Substituted Furo[3,2-c]pyridine N-Oxides: Synthesis and Reactions
Creators:
Bencková, Mária
Krutošíková, Alžbeta
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 3, pp. 539-547
Uncontrolled Keywords:Fused heterocycles, Furo[3,2-<i>c</i>]pyridines, <i>N</i>-Oxides, 1,3-Dipolar cycloadditions, Furo[3,2-<i>c</i>]pyrazolo[1,5-<i>a</i>]pyridines

Abstract

5-Aminofuro[3,2-<i>c</i>]pyridinium tosylates <strong>2a</strong>-<strong>2c</strong> were synthesized by direct <i>N</i>-amination of furo[3,2-<i>c</i>]pyridines <strong>1a</strong>-<strong>1c</strong> with <i>O</i>-(4-methylbenzenesulfonyl)hydroxylamine in dichloromethane. Zwitterionic furo[3,2-<i>c</i>]pyridinium <i>N</i>-imides <strong>3a</strong>-<strong>3c</strong> generated from <strong>2a</strong>-<strong>2c</strong> and anhydrous potassium carbonate in <i>N,N</i>-dimethylformamide afforded by 1,3-dipolar cycloaddition reactions with dimethyl butynedioate or ethyl propiolate the corresponding furo[3,2-<i>c</i>]pyrazolo[1,5-<i>a</i>]pyridinecarboxylic esters <strong>4a</strong>-<strong>4c</strong> and <strong>5a</strong>-<strong>5c</strong>. Furo[3,2-<i>c</i>]pyridine <i>N</i>-oxides <strong>6a</strong>-<strong>6c</strong> and their benzo derivative <strong>6d</strong> were synthesized by reaction of <strong>1</strong> with 3-chloroperbenzoic acid in dichloromethane. Treatment of <i>N</i>-oxides <strong>6</strong> with benzoyl chloride and cyanide anion (Reissert-Henze reaction) was shown to produce the corresponding furo[3,2-<i>c</i>]pyridine-4-carbonitriles <strong>7</strong>. In further transformations (acid and alkaline hydrolysis), the cyano group was converted successively to amide and carboxylic acid. <p>

Title:5-Aminofuro[3,2-c]pyridinium Tosylates and Substituted Furo[3,2-c]pyridine N-Oxides: Synthesis and Reactions
Creators:
Bencková, Mária
Krutošíková, Alžbeta
Uncontrolled Keywords:Fused heterocycles, Furo[3,2-<i>c</i>]pyridines, <i>N</i>-Oxides, 1,3-Dipolar cycloadditions, Furo[3,2-<i>c</i>]pyrazolo[1,5-<i>a</i>]pyridines
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:3
Page Range:pp. 539-547
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990539UNSPECIFIED
ID Code:1496
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Bencková, Mária; Krutošíková, Alžbeta (1999) 5-Aminofuro[3,2-c]pyridinium Tosylates and Substituted Furo[3,2-c]pyridine N-Oxides: Synthesis and Reactions. Collection of Czechoslovak Chemical Communications, 64 (3). pp. 539-547. ISSN 0010-0765

Repository Staff Only: item control page