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An Efficient Four‐component Reaction for the Synthesis of Spiroheterocyclic Compounds
Author(s) -
Meng Qinghua,
Xu Hui,
Xu Jing,
Hao Ganlu,
Gao Xu,
Hu Xiaoyu,
Rong LiangCe,
Cai Peijun
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2787
Subject(s) - chemistry , malononitrile , dioxolane , aryl , naphthalene , quinazoline , guanidine , amine gas treating , organic chemistry , reaction conditions , medicinal chemistry , aromatic amine , combinatorial chemistry , catalysis , alkyl
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.