Synthesis of 3,5-disubstituted pyridazines by regioselective [4+2] cycloadditions with ethynyltributyltin and subsequent replacement of the organotin substituent

Sauer, Jürgen and Heldmann, Dieter K. (1998) Synthesis of 3,5-disubstituted pyridazines by regioselective [4+2] cycloadditions with ethynyltributyltin and subsequent replacement of the organotin substituent. TETRAHEDRON, 54 (17). pp. 4297-4312. ISSN 0040-4020

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Abstract

Cycloadditions of 3-aryl-1,2,4,5-tetrazines 1a-o with ethynyltributyltin 5 occur with high regioselectivity to yield 3-aryl-5-tributylstannyl-pyridazines 9-23 in 71-95% yield. Moreover, the stannanes obtained could be utilized as starting materials for the preparation of various 3,5-disubstituted pyridazines as shown for 3-phenyl-5-tributylstannyl-pyridazine 9b. Stille cross-couplings with aryl halides yield 3,5-diaryl-pyridazines 26-29, whereas exposure to elemental halogens furnished 3-phenyl-5-halogeno-pyridazines 24 and 25, which can be used as starting compounds for further functionalizations like Heck reaction. (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 10:41
Last Modified: 24 Feb 2023 10:41
URI: https://pred.uni-regensburg.de/id/eprint/49892

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