Mupparapu Nagaraju, Khan Shahnawaz, Bandhoria Pankaj, Athimoolam Shunmuganarayanan, Ahmed Qazi Naveed
Medicinal Chemistry Division, Indian Institute of Integrative Medicine (IIIM), Jammu 180001, India.
Academy of Scientific and Innovative Research (AcSIR-IIIM), Jammu 180001, India.
ACS Omega. 2018 May 21;3(5):5445-5452. doi: 10.1021/acsomega.8b00715. eCollection 2018 May 31.
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.
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。
