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Yoshito Kishi (1937-2023)
Yoshito Kishi (1937-2023)
Professor. Yoshito Kishi,
a member of the Honorary Editorial Associates of HETEROCYCLES,
has passed away on January 9, 2023 at the age of 85.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
January 13, 2023
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Report | Regular issue | Vol 19, No. 7, 1982, pp.1269-1275
Published online, 1st January, 1970■ Selective Cleavage of Unsymmetrical 2,2-Spiro-1,3-dioxolanes. II. Cleavage of Ketal Ring of 5’-Bromo-6’,7’-dihydro-4-isopropylaminomethyl-1’-p-toluenesulfonyl-spiro[1,3-dioxolane-2,4’-(5H’)-indole and Its Analogs
Published online, 1st January, 1970
DOI: 10.3987/R-1982-07-1269
■ Selective Cleavage of Unsymmetrical 2,2-Spiro-1,3-dioxolanes. II. Cleavage of Ketal Ring of 5’-Bromo-6’,7’-dihydro-4-isopropylaminomethyl-1’-p-toluenesulfonyl-spiro[1,3-dioxolane-2,4’-(5H’)-indole and Its Analogs
Makiko Sakai
*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan
Abstract
The bromodioxolane and its analogs (1-5) were treated with organic base (DBU, DBN, or morpholine), acid (p-toluenesulfonic acid or Lewis acid), or Lewis acid/tertiary amine, and yielded 4-alkoxyindoles (6-17). Reaction of 1 with organic base gave two isomeric 4-alkoxyindoles, 6 (tosylpindolol, a secondary alcohol) and 11 (a primary alcohol), while tri-n-octylamine with stannic chloride afforded 6 (74 %) without producing 11.
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