Efficient synthesis of N-methoxyindoles via alkylative cycloaddition of nitrosoarenes with alkynes.
[reaction: see text] N-Methoxyindoles are produced in moderate to excellent yields from the reaction between nitrosoarenes and alkynes in the presence of K2CO3/(CH3)2SO4. Terminal alkynes with conjugating substituents afford 3-substituted N-methoxyindoles exclusively. The analogous reactions with methyl propiolate provide a one-step preparation of phytoalexin analogues from Wasabi.
Penoni
Andrea
A
Dipartimento di Scienze Chimiche ed Ambientali, Università degli Studi dell'Insubria, via Valleggio 11, 22100, Como, Italy. andrea.penoni@uninsubria.it
Palmisano
Giovanni
G
Broggini
Gianluigi
G
Kadowaki
Ayako
A
Nicholas
Kenneth M
KM
D000478:Alkylation; D000480:Alkynes; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation
D000480:Alkynes; D007202:Indicators and Reagents; D007211:Indoles; D047028:Macrocyclic Compounds