Preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines by a one-step reaction of 1,2,4-triazines with 1,2-dehydrobenzene

An original and convenient procedure has been proposed for one-step preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines in up to 40% yields via aza-Diels–Alder reaction of the readily available 3-dichloromethyl- and 3-trichloromethyl-1,2,4-triazines (in the role of dienes) with 1,2-d...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2019-11, Vol.55 (11), p.1124-1127
Main Authors: Nikonov, Igor L., Slepukhin, Pavel A., Kopchuk, Dmitry S., Kovalev, Igor S., Zyryanov, Grigory V., Suvorova, Anna I., Eltsov, Oleg S., Rusinov, Vladimir L., Chupakhin, Oleg N.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary:An original and convenient procedure has been proposed for one-step preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines in up to 40% yields via aza-Diels–Alder reaction of the readily available 3-dichloromethyl- and 3-trichloromethyl-1,2,4-triazines (in the role of dienes) with 1,2-dehydrobenzene (in the role of in situ generated dienophile). The structure of 1-trichloromethyl-4-phenylisoquinoline was confirmed by X-ray structural analysis.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-019-02588-1