An approach to cyclohepta[b]indoles through an allenamide (4 + 3) cycloaddition-Grignard cyclization-Chugaev elimination sequence.
A strategy for synthesizing highly functionalized cyclohepta[b]indoles through a concise (4 + 3) cycloaddition-cyclization-elimination sequence is described. The cycloaddition features nitrogen-stabilized oxyallyl cations derived from epoxidations of N-aryl-N-sulfonyl-substituted allenamides, while the cyclization and elimination employed an intramolecular Grignard addition and a one-step Chugaev process, respectively.
Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States.
Shuzhong
S
He
Richard P
RP
Hsung
William R
WR
Presser
Zhi-Xiong
ZX
Ma
Bryan J
BJ
Haugen
D003500:Cyclization; D061565:Cycloaddition Reaction; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles; D009584:Nitrogen