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Synthesis of indole and indolenine derivatives starting from indoline-2-thiones

✍ Scribed by Takehiko Nishio; Osamu Saku; Hiroshi Yamamoto

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
48 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Indoline‐2‐thiones 1a‐b,d,f,h, which have at least one hydrogen at the 3‐position reacted with α‐halo ester 2a‐d, α‐halo ketones 2e‐f, and a‐bromoacetonitrile 2g to give 2‐alkylthioindole derivatives 3–11. In a similar manner treatment of 3,3‐disubstituted indoline‐2‐thiones 1c,e with α‐halo esters 2a,c,d and α‐halo ketone 2e gave 2‐alkylthioindolenines 12–16. Treatment of 1,3,3‐ trisubstituted indoline‐2‐thiones 1g,i with ethyl bromo‐acetate 2a resulted in recovery of starting materials. Desulfurization of indolenine 14 with triphenylphosphine gave 2‐alkylideneindoline 19.

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Synthesis of Indole Derivatives by [2 +
Synthesis of Indole Derivatives by [2 + 2] Photocycloaddition of Indoline-2-thiones with alkenes and photodesulfurization of indoline-2-thiones
✍ Takehiko Nishio; Mitsuru Oka 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 German ⚖ 606 KB

The photochemical synthesis of indole derivatives starting from the indoline-2-thiones 1 is described. Irradiation of indoline-2-thiones 1 in the presence of alkenes 3 gave 2-alkyl-3H-indoles 4-7 or 2-alkylindoles 8-22 through the ring cleavage of the intermediates, spirocyclic amino-thietanes, init