|
|
|
Synthesis of Novel Spirooxindole and Spirodihydroqinoline by Domino [3+2] Cycloaddition and Acetylenedicarboxylate Promoted Ring-expansion Reaction |
ZHU MeiJun1, WU Wentao2, HAN Ying2, YAN Chaoguo2*
|
| 1. Jianghai Polytechnic College, Yangzhou 225101, China; 2. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China |
|
|
|
|
Abstract Multicomponent reaction and domino reaction are widely used in organic synthesis because of their using readily available raw materials, convenient synthetic method, less reaction steps and separation processes. a simple and efficient method for synthesizing spiro compounds via domino reaction was reported in this paper. The one-pot [3+2] cycloaddition reaction of L-thioproline, isatins and chalcones and sequential ring-expansion reaction with dimethyl but-2-ynedioate in refluxing methanol resulted in sulfanyl-containing polycyclic spirooxindole and spirodihydroqinoline derivatives. The spiro compounds were characterized by IR, HR-MS, 1H and 13C NMR spectroscopy and were confirmed by single crystal structures. The formation mechanism of the two compounds included domino ring-opening and annulation process. This reaction has the advantages of using readily available substrates, simple operation and high atomic economy.
|
|
Received: 27 March 2022
|
|
|
|
|
|
|
