Chemistry of N-chloronortropine derivatives: Synthesis of a bridged aziridine compound and new tropane derivatives

Syuichi Furuya; Toshihiko Okamoto

doi:10.3987/COM-88-4668

Chemistry of N-chloronortropine derivatives: Synthesis of a bridged aziridine compound and new tropane derivatives

Syuichi Furuya, Toshihiko Okamoto

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

An unsymmetrical bridged aziridine compound was obtained from N-chloronortropinone. This compound was found to react with acyl halides, acid anhydrides, and other reagents, including a Michael acceptor, dimethyl acetylenedicarboxylate (DMAD), giving new tropane bases with a ketone functional group at the bridged ethylene moiety. In the case of Michael-type addition, the retention of the aziridine ring system was observed in some solvents.

Original language	English
Pages (from-to)	2609-2618
Number of pages	10
Journal	Heterocycles
Volume	27
Issue number	11
DOIs	https://doi.org/10.3987/COM-88-4668
Publication status	Published - Nov 1988
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "An unsymmetrical bridged aziridine compound was obtained from N-chloronortropinone. This compound was found to react with acyl halides, acid anhydrides, and other reagents, including a Michael acceptor, dimethyl acetylenedicarboxylate (DMAD), giving new tropane bases with a ketone functional group at the bridged ethylene moiety. In the case of Michael-type addition, the retention of the aziridine ring system was observed in some solvents.",

author = "Syuichi Furuya and Toshihiko Okamoto",

year = "1988",

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doi = "10.3987/COM-88-4668",

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AU - Okamoto, Toshihiko

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Y1 - 1988/11

N2 - An unsymmetrical bridged aziridine compound was obtained from N-chloronortropinone. This compound was found to react with acyl halides, acid anhydrides, and other reagents, including a Michael acceptor, dimethyl acetylenedicarboxylate (DMAD), giving new tropane bases with a ketone functional group at the bridged ethylene moiety. In the case of Michael-type addition, the retention of the aziridine ring system was observed in some solvents.

AB - An unsymmetrical bridged aziridine compound was obtained from N-chloronortropinone. This compound was found to react with acyl halides, acid anhydrides, and other reagents, including a Michael acceptor, dimethyl acetylenedicarboxylate (DMAD), giving new tropane bases with a ketone functional group at the bridged ethylene moiety. In the case of Michael-type addition, the retention of the aziridine ring system was observed in some solvents.

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Chemistry of N-chloronortropine derivatives: Synthesis of a bridged aziridine compound and new tropane derivatives

Abstract

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