Studies with condensed amino-thiophenes: Further investigation of reactivity of amino-thieno-coumarines and amino-thieno-benzo[h]coumarines toward electron-poor olefins and acetylenes

✍ Scribed by Mervat M. Abdelkhalik; Abdalla M. Negm; Ayatt I. Elkhouly; Mohammed H. Elnagdi

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 107 KB
• Volume: 15
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20047

✦ Synopsis

Abstract

The reaction of 3‐amino‐5‐oxa‐2‐thia‐cyclopenta[a]naphthalene‐4‐one 2b with substituted acetylenes afforded C‐1 alkylation products. On the other hand, reaction of 17‐amino‐15‐methyl‐11‐oxa‐16‐thiacyclopenta[a]phenanthrene‐12‐one 5 with substituted acetylenes and electron‐poor olefins afforded the condensed thienopyridine derivatives 7 and 11a–c. The reaction of 5 with acrylonitrile and with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione afforded compounds 13 and 21 with loss of H~2~S via the expected [4 + 2] cycloaddition sequence. © 2004 Wiley Periodicals, Inc. Heteroatom Chem 15:502–507, 2004; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20047