One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α-Oxo-acetamidines

Abstract

A cesium carbonate promoted three-component reaction of N-H containing heterocycles, primary or secondary amines, arylglyoxaldehydes, and anilines is reported. The key step involves a tandem sequence of N-1 addition of a heterocycle or an amine to preformed α-iminoketones, followed by an air- or oxygen-mediated oxidation to form α-oxo-acetamidines. The scope of the reaction is enticingly broad, and this novel methodology is applied toward the synthesis of various polycyclic heterocycles.

Structure and Reactivity of Glycosyl Isocyanides

“…Thus, we performed an U‐3CR on the indole‐based imines yielding compounds 14a – e . Then, utilizing phenyl glyoxal in a Passerini reaction, we were able to synthesize compound 15 which could be transformed to a variety of derivatives . In addition, we performed a Passerini reaction with keto‐carboxylic acids affording the corresponding γ‐ and δ‐lactone derivatives 16a , b .…”

“…Then, utilizing phenyl glyoxal in a Passerini reaction, we were able to synthesize compound 15 which could be transformed to a variety of derivatives. [35][36][37] In addition, we performed a Passerini reaction with keto-carboxylic acids affording the corresponding γand δ-lactone derivatives 16a,b. In the cases of compounds 14 and 15, we obtained the epimeric mixture…”

Highly Efficient Copper-Catalyzed Dehydrogenative Cross-Coupling of Azoles with α-Amino Carbonyl Compounds

“…Unless otherwise indicated, all reagents were purchased from commercial distributors and used without further purification. 1 H NMR and 13 C NMR spectra were recorded at 400 or 500 MHz and 100 or 125 MHz, respectively, using tetramethylsilane as an internal reference. High-resolution mass spectra (HRMS) were measured with a quadrupole time-of-flight (Q-TOF) mass spectrometer instrument with an electrospray ionization (ESI) source.…”

“…1 H NMR (400 MHz, CDCl 3 ):  = 8.59-8.45 (m, 1 H), 8.09 (s, 1 H), 7.92-7.83 (m, 1 H), 7.79 (d, J = 7.6 Hz, 2 H), 7.56 (t, J = 7.2 Hz, 1 H), 7.48-7.35 (m, 4 H), 7.06 (d, J = 7.2 Hz, 1 H), 6.92 (dt, J = 20.8, 7.2 Hz, 2 H), 6.74 (d, J = 7.6 Hz, 1 H), 2.33 (s, 3 H). 13 C NNMR (100 MHz, CDCl 3 ):  = 190.3, 148.2, 144.3, 143.9, 141.5, 135.5, 133.8, 131.7, 130.5, 129.9, 129.2, 129.2, 126.2, 125.4, 124.9, 120.7, 120.0, 115.9, 18.…”

Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds

“…Heterocyclic compounds are very important organic compounds widely used in the elds of medicine, 36 pesticides, 37 and other materials that are synthesized by MCRs. 38,39 PILC-1 was rst used to catalyst threecomponent reactions in an acetonitrile, ethanol, and THF system (Table 3). Interesting, catalytic activity and enantioselectivity were the highest for the PILC-1 in ethanol as it had the optimal conversion (79%) and ee value (91%) among the solvents (Table 3, To determine the effect of different structures on the catalytic properties of PILCs, three component reactions were carried out with different catalyst systems (Table 4).…”