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Unexpected Brønsted Acid‐Catalyzed Domino Reaction of 3‐Hydroxyisoindolin‐1‐ones and N ‐ tert ‐Butyl Hydrazones for the Synthesis of 3‐(Hydrazono)isoindolin‐1‐ones
Author(s) -
Chen HuiXuan,
Li Yongsu,
He Xuefeng,
Zhang Yaqi,
He Wenhuan,
Liang Hao,
Zhang Yuyang,
Jiang Xiaoding,
Chen Xiangmeng,
Cao Rihui,
Liu GaoFeng,
Qiu Liqin
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801293
Subject(s) - chemistry , hydrazone , trifluoroacetic acid , catalysis , domino , brønsted–lowry acid–base theory , medicinal chemistry , phosphoric acid , cascade reaction , mannich reaction , organic chemistry
A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N ‐ tert ‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)isoindolin‐1‐one derivatives in excellent yields with high chemoselectivities. The E ‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction of 5w .