Ethynyltributyltin - a synthetic equivalent for acetylene, aryl, acyl and halogeno alkynes in [4+2] cycloadditions

Sauer, Jürgen and Heldmann, Dieter K. (1998) Ethynyltributyltin - a synthetic equivalent for acetylene, aryl, acyl and halogeno alkynes in [4+2] cycloadditions. TETRAHEDRON LETTERS, 39 (17). pp. 2549-2552. ISSN 0040-4039

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Abstract

Ethynyltributyltin 2 cycloadds to 5-phenyl-1,2,4-triazine-3-carboxyclic acid methyl ester 1 to furnish mainly 4-tributylstannyl-6-phenyl-pyridine-2-carboxyclic acid methyl ester 3a besides a small amount of the 3-tributyistannyl isomer 3b. The tributyltin substituent of pyridine 3a can be replaced by Pd-catalyzed acylation and arylation, by halogenation and protonation to yield functionalized pyridines 4-7, which are not available by direct cycloaddition of the corresponding alkynes. (C) 1998 Elsevier Science Ltd. All rights reserved.

Item Type: Article
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 24 Feb 2023 10:43
Last Modified: 24 Feb 2023 10:43
URI: https://pred.uni-regensburg.de/id/eprint/49893

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