NitroketeneN,S-acetals: synergistic building blocks for the synthesis of heterocycles

Abstract

This review highlights the synthesis of several kinds of nitroketene N,S-acetals and their applications in the synthesis of different kinds of heterocyclic compounds.

Recent synthetic strategies of spiro-azetidin-2-one, -pyrrolidine, -indol(one) and -pyran derivatives-a review

“…100 (E)-N-Methyl-1-(methylthio)-2-nitroethenamine (NMSM) (208) has drawn signicant attention as an important synergistic building block due to the presence of push-pull skeleton for the synthesis of various O/N-heterocyclic ring systems via multicomponent reactions (MCRs). 101,102 By using an MCR strategy and NMSM as a building block, spiro-4H-pyrans were synthesized using oxygen containing 1,3-dinucleophilic sources (cyclic-1,3-diketone, 209), isatin derivatives 71, and 1N-methyl-1S-methyl-2-nitroethylene (NMSM) 208 under catalyst-free conditions to furnish compounds 210 (Scheme 55). 102 These compounds were initially screened for in vitro antibacterial Generally, arylideneindolinones 110 bearing either electrondonating or electron-withdrawing groups at the 5-or 6-position provided good yields.…”

Acid-Mediated Synthesis of Chromeno[2,3-b]pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives

“…The rich reaction sites render NMSM broad application prospects in the construction of heterocyclic compounds in organic and pharmaceutical chemistry. 13 For instance, H 2 receptor antagonists nizatidine 14 and ranitidine 15 were both prepared from NMSM. In our previous work, diverse heterocyclic compounds have been constructed by a series of nitroalkenes as the building blocks.…”

α-Aminoazoles/azines: key reaction partners for multicomponent reactions

“…The beginning of the 21st century marked an increase in the interest in multicomponent reactions (MCRs) as a highly impressive tool to access elaborate molecular scaffolds, while combining structural diversity with eco-compatibility to achieve the diversity-orientated synthesis of a variety of molecules, especially bioactive heterocycles. 11 MCRs are now well-established convergent chemical approaches, in which a single operation is sufficient to build one product from the well-defined condensation of three or more reactant molecules with high atom economy and multiple-bond-forming efficiency. 12 With a reduced number of reaction steps and starting from simple, inexpensive starting materials, MCRs render the library production of substantially diverse range of small molecules less costly compared to conventional approaches.…”