Synthesis of 3-aroylindoles as intermediates of cannabimimetics and elucidation of their physicochemical properties

Koji Araki; Kosho Makino; Hidetsugu Tabata; Hiroshi Nakayama; Kei Zaitsu; Tetsuta Oshitari; Hideaki Natsugari; Hideyo Takahashi

doi:10.3987/COM-18-13888

Synthesis of 3-aroylindoles as intermediates of cannabimimetics and elucidation of their physicochemical properties

Koji Araki, Kosho Makino, Hidetsugu Tabata, Hiroshi Nakayama, Kei Zaitsu, Tetsuta Oshitari, Hideaki Natsugari, Hideyo Takahashi

Faculty of Pharmaceutical Sciences

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

2 Scopus citations

Abstract

In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the¹H NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.

Original language	English
Pages (from-to)	910-920
Number of pages	11
Journal	Heterocycles
Volume	96
Issue number	5
DOIs	https://doi.org/10.3987/COM-18-13888
State	Published - 2018

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title = "Synthesis of 3-aroylindoles as intermediates of cannabimimetics and elucidation of their physicochemical properties",

abstract = "In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the1H NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.",

author = "Koji Araki and Kosho Makino and Hidetsugu Tabata and Hiroshi Nakayama and Kei Zaitsu and Tetsuta Oshitari and Hideaki Natsugari and Hideyo Takahashi",

note = "Publisher Copyright: {\textcopyright} 2018 The Japan Institute of Heterocyclic Chemistry.",

year = "2018",

doi = "10.3987/COM-18-13888",

language = "英語",

volume = "96",

pages = "910--920",

journal = "Heterocycles",

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T1 - Synthesis of 3-aroylindoles as intermediates of cannabimimetics and elucidation of their physicochemical properties

AU - Araki, Koji

AU - Makino, Kosho

AU - Tabata, Hidetsugu

AU - Nakayama, Hiroshi

AU - Zaitsu, Kei

AU - Oshitari, Tetsuta

AU - Natsugari, Hideaki

AU - Takahashi, Hideyo

PY - 2018

Y1 - 2018

N2 - In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the1H NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.

AB - In order to synthesize the intermediates of cannabimimetics, the benzoylation of indoles with 2'/3'/4'-substituted benzoyl chloride in the presence of Et2AlCl was examined. Among the products, we found that the1H NMR spectra of 3-(2'-substituted)-benzoyl-2-methylindoles had interesting features. We investigated their physicochemical properties based on VT-NMR, and it was revealed that conformer A (s-trans) is present in preference to conformer B in these compounds.

UR - https://www.scopus.com/pages/publications/85047943768

U2 - 10.3987/COM-18-13888

DO - 10.3987/COM-18-13888

M3 - 記事

AN - SCOPUS:85047943768

SN - 0385-5414

VL - 96

SP - 910

EP - 920

JO - Heterocycles

JF - Heterocycles

IS - 5

ER -

Synthesis of 3-aroylindoles as intermediates of cannabimimetics and elucidation of their physicochemical properties

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