- Preparation of 3-diazoindolin-2-imines via cascade reaction between indoles and sulfonylazides and their extensions to 2,3-diaminoindoles and imidazo[4,5-b]indoles.
Preparation of 3-diazoindolin-2-imines via cascade reaction between indoles and sulfonylazides and their extensions to 2,3-diaminoindoles and imidazo[4,5-b]indoles.
Organic letters (2014-09-12)
Guorong Sheng, Kai Huang, Zhihao Chi, Hualong Ding, Yanpeng Xing, Ping Lu, Yanguang Wang
PMID25211289
ABSTRACT
3-Diazoindolin-2-imines were constructed from indoles and sulfonylazides via an electronically matched 1,3-dipolar cycloaddition and a subsequent dehydroaromatization/ring-opening cascade. The reaction between 3-substituted indoles and sulfonyl azides provided 2-aminoindoles, while 2-substituted indoles furnished 3-aminoindoles. Moreover, 2,3-diaminoindoles could be prepared from the resulting 3-diazoindolin-2-imines and secondary amines via a rhodium-catalyzed amination. Further extension of 2,3-diaminoindoles led to the formation of imidazo[4,5-b]indoles.
MATERIALS
Product Number
Brand
Product Description
Rhodium, wire reel, 0.1m, diameter 1.0mm, as drawn, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.12mm, as drawn, 99.9%
Rhodium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, x-ray quality, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.2m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.05m, diameter 0.5mm, as drawn, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.50μm, specific density 620μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, wire reel, 0.2m, diameter 0.12mm, as drawn, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 25x25mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%
Rhodium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%
Rhodium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%
Rhodium, foil, not light tested, 10x10mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.0005mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, wire reel, 0.5m, diameter 0.12mm, as drawn, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.5m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, wire reel, 0.1m, diameter 0.12mm, as drawn, 99.9%
Rhodium, foil, light tested, 15x15mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.9%