一锅串联法合成功能化3-羟基-2-呋喃基丙烯酰胺
One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides.
作者信息
Mupparapu Nagaraju, Khan Shahnawaz, Bandhoria Pankaj, Athimoolam Shunmuganarayanan, Ahmed Qazi Naveed
机构信息
Medicinal Chemistry Division, Indian Institute of Integrative Medicine (IIIM), Jammu 180001, India.
Academy of Scientific and Innovative Research (AcSIR-IIIM), Jammu 180001, India.
出版信息
ACS Omega. 2018 May 21;3(5):5445-5452. doi: 10.1021/acsomega.8b00715. eCollection 2018 May 31.
Abstract
A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal-Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O-H···O hydrogen bond between hydroxyl and carbonyl O atoms leading to self-associated ()-2-furanyl-acrylamides.
摘要
提出了一种新颖的一锅串联反应，该反应涉及Knoevenagel缩合、迈克尔加成、选择性酰胺化以及Paal-Knorr环化反应，可从简单的2-氧代醛和芳酰基乙腈制备各种功能化的3-羟基-2-呋喃基丙烯酰胺。还尝试将反应范围扩展到不同的2-杂芳基呋喃。沿晶胞α轴向下观察分子的堆积图显示，羟基和羰基O原子之间存在特征性的分子内经典O-H···O氢键，导致形成自缔合的()-2-呋喃基丙烯酰胺。
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