Journal
ORGANIC LETTERS
Volume 18, Issue 22, Pages 5884-5887Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b02965
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Funding
- National Science Foundation [CHE-1464690]
- National Science Foundation of China [21602148]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1559715] Funding Source: National Science Foundation
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Catalyst-dependent [4 + 2]-cycloaddition reactions of azoalkenes from alpha-halohydrazones with enol diazoacetates have been developed. A [4 + 2]-cydoaddition of enol diazoacetates with in situ formed azoalkenes produces tetrahydropyridazinyl-substituted diazoacetates promoted by only Cs2CO3. In contrast, donor acceptor cyclopropenes, which are formed in situ from enol diazoacetates by Rh-2(OAc)(4)-catalyzed dinitrogen extrusion, undergo [4 + 2]-cycloaddition with azoalkenes to yield bicyclo[4.1.0]tetrahydropyridazines. These stable cycloaddition products undergo subsequent one-step transformations to form 6-alkylidenetetrahydropyridazines and 4,5,6,7-tetrahydro-1,2-diazepine derivatives in good yields.
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