DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives

• Soumitra Guin,
• Raman Gupta,
• Debashis Majee and
• Sampak Samanta

Beilstein J. Org. Chem. 2018, 14, 2771–2778, doi:10.3762/bjoc.14.254

• nicotinonitriles has been also greatly explored in the literature [56][57]. Even though great progress, the synthesis of (2-hydroxyaryl)pyridines bearing a CO2Et/CN group at C3 position remains a daunting task in synthetic organic chemistry [58][59]. A literature study reveals that a lot of research is focused on

• cyclic sulfamidate imines and MBH acetates of acrylate as coupling partners [68]. Herein, we further present a DABCO-catalyzed and DBU-promoted sequential one-pot procedure for the access to the interesting class of (2-hydroxyaryl)nicotinates/nicotinonitriles from N-sulfonyl ketimines and MBH adducts as

• . Next, we further expanded our present methodology for the synthesis of 2-hydroxyarylated nicotinonitriles by using MBH carbonates derived from an acrylonitrile. Experimental data revealed that several aryl-substituted MBH carbonates 2k–2m underwent [3 + 3] cyclization with N-sulfonyl ketimines 1a and

Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine

• Ashley R. Longstreet,
• Suzanne M. Opalka,
• Brian S. Campbell,
• B. Frank Gupton and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2013, 9, 2570–2578, doi:10.3762/bjoc.9.292

• ; nicotinonitriles; Introduction Nevirapine (3) was the first commercially available non-nucleoside reverse transcriptase inhibitor (NNRTI), and has remained an important medicine in the management of human immunodeficiency virus (HIV) [1][2]. Nevirapine combined with lamivudine (3TC) and azidothymidine (AZT) or

• dimethyl acetal (DMF-DMA) [34]. Previous attempts to synthesize the nicotinonitriles via enamines resulted in poor yields due to dimerization of the starting alkylidene malononitrile [35][36][37]. A high yield enamine approach allows us to begin the synthesis from the commodity chemicals (acetone and

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

• Mark C. Bagley,
• Vincenzo Fusillo,
• Robert L. Jenkins,
• M. Caterina Lubinu and
• Christopher Mason

Beilstein J. Org. Chem. 2013, 9, 1957–1968, doi:10.3762/bjoc.9.232

• process, a phenomenon that has also been observed for two-step-in-one Bohlmann–Rahtz reactions [54], in the Michael addition of ethynyl ketones [51], both under conductive heating, and in the tandem oxidation Bohlmann–Rahtz synthesis of nicotinonitriles under microwave irradiation [59]. These batch