ISSN:
0170-2041
Keywords:
1-(Dimethylamino)-1-buten-3-yne, Vilsmeier addition to
;
Glutaconaldehyde derivatives, 3-substituted
;
1-Methoxy-1-buten-3-yne, Vilsmeier addition to
;
1-Methoxy-1-penten-3-yne, Vilsmeier addition to
;
Pentamethinium salts, 3-substituted
;
Vilsmeier addition to butenynes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses with Aliphatic Dialdehydes, XLV. - Substituted Glutaconaldehyde Derivatives by Vilsmeier Addition to 1-Methoxy-1-buten-3-yne, 1-Methoxy-1-penten-3-yne, and 1-(Dimethylamino)-1-buten-3-yne and Their Reactions with Some Nucleophiles3-Halogeno-substituted unsymmetrical pentamethinium salts 5, 7, 8, and 10 as well as 3-halogeno-substituted symmetrical vinamidinium salts 6, 9, and 11 are synthesized by addition of suitably substituted Vilsmeier reagents to 1-methoxy-1-buten-3-yne (1). Analogous Vilsmeier additions to 1-methoxy-1-penten-3-yne lead to 3-halogen-2-methyl-substituted unsymmetrical pentamethinium salts 13 and 14. Symmetrical 3-methoxy-and 3-methylthio-substituted vinamidinium salts 15 and 16 are observed by appropriate Vilsmeier additions to 1-(dimethylamino)-1-buten-3-yne (4). Further 3-substituted unsymmetrical and symmetrical pentamethinium salts are obtained by nucleophilic substitution at the C-3 position of these salts, leading to 19-27. The [C4 + C1] pathway to 3-substituted glutaconaldehyde derivatives represents a useful completion to their synthesis.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199119910121
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