Journal article

Simple thiazocine-2-acetic acid derivatives via ring-closing metathesis.

Bates D, Li X, Jog P ...see all

The Journal of organic chemistry, vol. 69, issue 8 (2004) pp. 2750-4

  • 3


    Mendeley users who have this article in their library.
  • 20


    Citations of this article.
Sign in to save reference


A new protocol for synthesis of 2-heterocylylacetic acid derivatives involving conjugate addition of allyl mercaptan to an acrylate containing a tethered olefinic site followed by RCM (ring-closing metathesis) is described. In this series, sulfanyl derivatives were unreactive, while sulfoxide and sulfone analogues provided the corresponding thiazocines in fair to excellent yields. Use of the sulfoxide oxidation state as a protecting group for sulfides inert to RCM is demonstrated also. Thus, oxidation of sulfide 9 [N-allyl-N-[2-(allylthio)-4-(1H-indol-1-yl)-4-oxobutyl]-4-methylbenzenesulfonamide] followed by cyclization yielded the corresponding thiazocine sulfoxide 12. Deprotection (deoxygenation) of 12 was accomplished using Lawesson's reagent, producing 1-[[4-[4-(methylphenyl)sulfonyl]-3,4,5,8-tetrahydro-2H-1,4-thiazocin-2-yl]acetyl]-1H-indole (21) in 67% unoptimized yield.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Get full text


  • Dallas K Bates

  • Xiaofen Li

  • Parag V Jog

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free