Ascorbic Acid-Initiated Tandem Radical Cyclization of N-Arylacrylamides to Give 3,3-Disubstituted Oxindoles.
An ascorbic acid-promoted and metal-free tandem room temperature cyclization of N-arylacrylamides with 4-nitrobenzenediazonium generated in situ was developed. This reaction proceeds smoothly through a radical mechanism and provides an environmentally friendly alternative approach to biologically active 3-alkyl-3-benzyloxindoles, avoiding the use of excess oxidants and light irradiation.
Hunan Co-Innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128, China. shengliu21@163.com.
Sheng
S
Liu
Hunan Co-Innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128, China. picheng55@126.com.|Pre-State Key Laboratory for Germplasm Innovation and Utilization of Crop, Hunan Agricultural University, Changsha 410128, China. picheng55@126.com.
Pi
P
Cheng
Hunan Co-Innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128, China. lwhncs618@163.com.
Wei
W
Liu
Hunan Co-Innovation Center for Utilization of Botanicals Functional Ingredients, Hunan Agricultural University, Changsha 410128, China. ginkgo@world-way.net.|Pre-State Key Laboratory for Germplasm Innovation and Utilization of Crop, Hunan Agricultural University, Changsha 410128, China. ginkgo@world-way.net.
Jian-Guo
JG
Zeng
D000178:Acrylamides / Q000737:chemistry*; D001205:Ascorbic Acid / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles
D000178:Acrylamides; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D001205:Ascorbic Acid
3,3-disubstituted oxindoles; 4-nitroaniline; N-arylacrylamides; ascorbic acid; tandem cyclization