Intramolecular Ritter Reactions of 2‐(2‐Cyanoethyl)tetrahydrocyclopenta[b]indole and ‐carbazole Derivatives

Abstract

Intramolecular Ritter reactions of 2-(2-cyanoethyl)tetrahydrocyclopenta [b]indole and -carbazole derivatives, prepared by a sequence of two different α-substitutions and Grignard reactions of the indole-based ketones 4-methyl-1,4-dihydrocyclopenta [b]indol-3(2H)-one and 9-methyl-2,3,4,9-tetra-

Metal-organic framework MIL-53(Al): synthesis, catalytic performance for the Friedel-Crafts acylation, and reaction mechanism

“…At first, the Al 3+ of MIL-53(Al) participates in the direct bonding of the benzoyl chloride (1) to form activated complex (2), after which this unstable complex converts to an acylium ion (3). Next, a nucleophile indole (4) attacks the acyl ion (3) and an electrophilic substitution reaction occurs to generate the indole intermediate (5). After the charge transfer to the chlorine ion occurs, the HCl and product 3-acylindole (7) is formed.…”

“…Thus, the synthesis of 3-acylindoles has gained considerable attention among heterocyclic organic chemists [3]. Traditionally, a wide variety of 3-acylindoles have been prepared by several well-known methods such as VilsmeierHaack type reaction [4], Grignard reactions [5], and FriedelCrafts acylations. The Vilsmeier-Haack type reaction is simple and can achieve high yields, but its application ranges are restricted and are only suitable for active substrate.…”

Incorporation of an indole-containing diarylbutylamine pharmacophore into furo[2,3-a]carbazole ring systems

“…7,8 b-Keto ester 10 was prepared by treatment of 9 with potassium hydride and dimethyl carbonate. 9 Subsequent allylation gave the 2-allyl-1-oxo-1H-carbazole-2-carboxylate 11, which was submitted to a Grignard reaction with freshly prepared PhMgBr. Following chromatographic purification alcohol 12 was isolated as the major diastereoisomer with a d.e.…”

Synthesis of Cycloalk[b]indole Bearing Spiropiperidine Derivatives

“…The synthesis of spiropiperidinone and spiropiperidinedione structures was performed by a new method [13][14][15]. For this aim, we used easily available compounds 1a-c and 6a-c as starting compounds and synthesized according to the literature [16][17][18][19][20]. The β-ketoesters (2a, 2b, 2c, 7a [20], 7b [21], and 7c) were prepared with the condensation reaction between keto compounds (1a-c and 6a-c) and diethyl carbonate in the presence of potassium hydride [21,22].…”