Three-component reaction of azulene, aryl glyoxal and 1,3-dicarbonyl compound for the synthesis of various azulene derivatives

Abstract

Three-component reaction of azulene, aryl glyoxal and 1,3-dicarbonyl compound and subsequent post-transformations provide access to three distinct types of azulene derivatives.

Simple and efficient synthesis of pyrrolo[3,2‐f]quinoxaline derivatives via three‐component reaction

“…After the successful utilization of dimedone, we next extended our investigation to cyclohexane-1,3-dione (3b). To our delight, cyclohexane-1,3-dione could also be successfully engaged in these MCRs and the corresponding pyrrolo[3,2-f]quinoxaline derivatives were provided with 72-90% yields (entries [13][14][15][16][17][18][19].…”

“…Recently, many research groups investigated the preparation of novel nitrogen-containing heterocycles by the reaction of the amines, arylglyoxals, and nucleophilic reagents through multicomponent reactions [17][18][19][20][21][22][23]. In 2020, we developed a three-component reaction of quinoxalin-6-amine, aldehyde, and 1,3-dicarbonyl compounds in EtOH solvent, yielding pyrazino[2,3-a]acridine derivatives [24].…”

Divergent synthesis of two types of indolizines from pyridine-2-acetonitrile, (hetero)arylglyoxal, and TMSCN

“…Our initial attempts to prepare 5 via one-pot three-component coupling of pyridine-2-acetonitrile, phenylglyoxal, 8 and TMSCN under similar conditions to the ones for 1 and 3 led us to different outcomes. The reaction of pyridine-2-acetonitrile, phenylglyoxal (2.5 equiv.…”

Azulene, Reactivity, and Scientific Interest Inversely Proportional to Ring Size; Part 1: The Five-Membered Ring

“…The next synthesis starts from the Knoevenagel condensation between aryl glyoxal and a 1,3-dicarbonyl compound, affording intermediate 58.1. The azulenes present in the reaction medium add to this intermediate, and in the last step a proton transfer in the intermediate 58.2 would produce the desired azulene derivative (Scheme 58) [102]. Depending on the reaction conditions and the structure of the starting materials, diketone 58.3 or ketoenol 58.4 results with the structure and yields described in Scheme 58.…”