Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 21, Pages 10692-10704Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4016908
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Funding
- National Natural Science Foundation of China [21272106, 20902040, J1103307]
- Changjiang Scholars and Innovative Research Team in University [IRT1138]
- 111 project
- Fundamental Research Funds for the Central Universities [lzujbky-2012-61, lzujbky-2013-ct02]
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The intramolecular addition of hydrazone radicals to carbon-carbon double bonds was achieved by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or DIAD (diisopropyl azodicarboxylate) as the hydrazone radical initiator as well as the carbon radical scavenger. Consequently, alkenes were difunctionalized to afford pyrazolines and tetrahydropyridazines via C-N forming S-exo-trig and 6-exo-trig cyclizations, respectively, and allyls were trifunctionalized to afford pyrazolines via C-N forming tandem 1,5-H-shift/S-exo-trig cyclizations under metal-free neutral conditions.
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