An Efficient Four‐component Reaction for the Synthesis of Spiroheterocyclic Compounds. (18th November 2016)

• Record Type: Journal Article
• Authors: Meng, Qinghua; Xu, Hui; Xu, Jing; Hao, Ganlu; Gao, Xu; Hu, Xiaoyu; Rong, Liang‐Ce; Cai, Peijun
• Is Part Of: Journal of heterocyclic chemistry. Volume 54:Number 3(2017:May)
• Page Start: 1925
• Page End: 1930
• Publication Date: 2016-11-18
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2787
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : A series of 6‐amino‐8‐aryl‐3, 4‐dihydro‐1 H ‐spiro[naphthalene‐2, 2'‐[1, 3] dioxolane]‐5, 7‐dicarbonitrile and 8‐arylidene‐4‐aryl‐7, 8‐dihydro‐5 H ‐spiro[quinazoline‐6, 2'‐[1, 3] dioxolan]‐2‐amine derivatives have been synthesized from the reactions of 1, 4‐dioxaspiro[4.5] decan‐8‐one, aromatic aldehydes, and malononitrile (or guanidine carbonate) under different conditions with high yields. In this research, it was found the DBU–THF was efficient reaction condition for obtaining 6‐amino‐8‐aryl‐3, 4‐dihydro‐1 H ‐spiro[naphthalene‐2, 2'‐[1, 3]dioxolane]‐5, 7‐dicarbonitrile derivatives, while 95% EtOH and NaOH was the preferred condition for the synthesis of 8‐rylidene‐4‐aryl‐7, 8‐dihydro‐5 H ‐spiro[quinazoline‐6, 2'‐[1, 3]dioxolan]‐2‐amine derivatives. To the best of our knowledge, these Spiroheterocycles were first reported in our research. The other advantages of this process were short‐reaction time, wide scope substrates, and simple set‐up. Abstract :