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

✍ Scribed by Jürgen Sauer; Dieter K. Heldmann

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 937 KB
Volume: 54
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(98)00127-6

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✦ Synopsis

Cycloadditions of 3-aryl-l,2.4,5-tetrazines la-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-allsubstituted pyridazines as shown for 3-phenyl-5-tributylstannyl-pyridazine 9b. Stifle ~couplings with aryl halides yield 3,5-diatyl-pyridazines 26-29, whereas exposure to elemental halogens furnished 3-phenyl-5-halogeno-pyridazines 24 end 25, which can be used as starting compounds for further functionalizations like Heck reaction.

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