Dichotomy in the Ring Opening Reaction of 5-[(2-Furyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione with Cyclic Secondary Amines

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Title:Dichotomy in the Ring Opening Reaction of 5-[(2-Furyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione with Cyclic Secondary Amines
Creators:
Šafář, Peter
Považanec, František
Prónayová, Naďa
Baran, Peter
Kickelbick, Guido
Kožíšek, Jozef
Breza, Martin
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 12, pp. 1911-1938
Uncontrolled Keywords:Substituted Meldrum's acids, Cyclizations, Furans, Cyclopentenones, Ring opening, 4<i>H</i>-1,3-Dioxines, Crystal structure, Reaction mechanisms, Amides

Abstract

5-[(2-Furyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (<strong>1a</strong>) treated with equimolar amount of pyrrolidine or hexahydroazepine afforded 5-(pyrrolidine)- (<strong>2a</strong>) or 5-[(hexahydro- azepine-1-yl)-2-hydroxypenta-2,4-dien-1-ylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (<strong>2d</strong>). Their treatment with hydrobromic acid led to cyclization and formation of stable 5-cyclopentenyl-4<i>H</i>-1,3-dioxine hydrobromides (<strong>3a</strong>, <strong>3d</strong>). Under the same conditions <strong>1a</strong> treated with morpholine or piperidine yielded a mixture of <strong>2b</strong>, <strong>3b</strong> and <strong>2c</strong>, <strong>3c</strong>, respectively. The corresponding 3-substituted furans <strong>1b</strong>-<strong>1e</strong> gave only substituted 5-cyclopentenyl-4<i>H</i>-1,3-dioxines (<strong>3e</strong>-<strong>3i</strong>). The use of an excess amine in reaction with <strong>1a</strong> yielded unexpectedly 5-(3,5-dihetaryl-cyclopent-2-en-1-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-diones (<strong>9a-9c</strong>) and 5-[5-hexahydroazepin-1-ium-1-ylidene-2-(hexahydroazepin-1-yl)cyclopent-1-en-1-yl]-2,2-dimethyl-4-oxo-4<i>H</i>-1,3-dioxin-6-olates (<strong>10</strong>). <p>

Title:Dichotomy in the Ring Opening Reaction of 5-[(2-Furyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione with Cyclic Secondary Amines
Creators:
Šafář, Peter
Považanec, František
Prónayová, Naďa
Baran, Peter
Kickelbick, Guido
Kožíšek, Jozef
Breza, Martin
Uncontrolled Keywords:Substituted Meldrum's acids, Cyclizations, Furans, Cyclopentenones, Ring opening, 4<i>H</i>-1,3-Dioxines, Crystal structure, Reaction mechanisms, Amides
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:65
Number:12
Page Range:pp. 1911-1938
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001911UNSPECIFIED
ID Code:1769
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Šafář, Peter; Považanec, František; Prónayová, Naďa; Baran, Peter; Kickelbick, Guido; Kožíšek, Jozef; Breza, Martin (2000) Dichotomy in the Ring Opening Reaction of 5-[(2-Furyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione with Cyclic Secondary Amines. Collection of Czechoslovak Chemical Communications, 65 (12). pp. 1911-1938. ISSN 0010-0765

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