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Catalyst‐Free Synthesis of 2,3‐Benzodiazepines via Tetrahydrodiazirino[3,1‐a]isoquinoline Reacts with Sulfonyl Chlorides
Author(s) -
Wang Kaikai,
Li Yanli,
Wang Xiaoyu,
Zhu Baoku
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900045
Subject(s) - isoquinoline , chemistry , sulfonyl , catalysis , medicinal chemistry , ring (chemistry) , aryl , alkyl , reaction conditions , combinatorial chemistry , organic chemistry
An unexpected process from tetrahydrodiazirino[3,1‐ a ]isoquinolines and diversified sulfonyl chlorides RSO 2 Cl (R=aryl, alkyl) to deliver highly yields 4,5‐dihydro‐3H‐benzo[ d ][1,2]diazepine skeleton compounds was disclosed via N ‐insertion ring‐opening reaction. The structural framework of 2,3‐benzodiazepines is unambiguously confirmed by single‐crystal X‐ray crystallographic analysis. The present protocol features mild reaction conditions, high yields and feasibility of large‐scale synthesis and catalyst‐free access to benzo[2,3]diazepines skeleton. In contrast, azomethine imines were produced by employing tetrahydrodiazirino[3,1‐ a ]isoquinoline reacts with aroyl chlorides under the same conditions.