Structure, electronic, spectroscopic and reactivity investigations of pharmacologically active compound 1–acetyl–3–indolecarboxaldehyde – An experimental and theoretical approach

Synthesis of N‐Acyl Indole‐3‐Carboxaldehyde Derivatives and Polyvinyl Alcohol Acetalization with 1‐Propionylindole‐3‐Carboxaldehyde

“…These spectra indicate the presence of an aldehydic C=O peak at 1659.09 cm −1 for derivative ( I) and (VII) , 1673.05 cm −1 for derivative ( II), (V) and (VI) , 1618.37 cm −1 for derivative ( III) and 1622.16 cm −1 for derivative ( IV) . Furthermore, all derivatives exhibit an amide carbonyl (−CONR 2 ) absorption at 1724.76 cm −1 , 1666.48 cm −1 and 1687.82 cm −1 , consistent with previous reports [15,38–40] . This confirms the formation of amide linkages between the −NH group of indole‐3‐carboxaldehyde and the −COCl group of various carboxylic acid chlorides.…”

“…Furthermore, all derivatives exhibit an amide carbonyl (À CONR 2 ) absorption at 1724.76 cm À 1 , 1666.48 cm À 1 and 1687.82 cm À 1 , consistent with previous reports. [15,[38][39][40] This confirms the formation of amide linkages between the À NH group of indole-3-carboxaldehyde and the À COCl group of various carboxylic acid chlorides. The CÀ H stretching vibrations for all derivatives were observed within the range of 2812.21 cm À 1 to 3126.27 cm À 1 .…”

“…Various N‐substituted derivatives of indoles were explored to protect the nitrogen atom and avoid unwanted oligomerization and addition reactions, resulting in a wide range of N‐acyl and N‐alkyl derivatives [14] . 1‐Acetyl‐3‐indolecarboxaldehyde and 1‐benzoyl‐1 H‐indole‐3‐carbaldehyde were synthesized in the presence of triethylamine and their structural and spectral characteristics were studied [15,16] . Markgraf et al.…”

“…[14] 1-Acetyl-3-indolecarboxaldehyde and 1-benzoyl-1 H-indole-3-carbaldehyde were synthesized in the presence of triethylamine and their structural and spectral characteristics were studied. [15,16] Markgraf et al used DCC along with a small quantity of DMAP to facilitate reaction between indole-3-carboxaldehyde and 4-pentynoic acid. [17] DMAP is considered a good acetylating agent for increasing the reaction rate.…”

The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives

“…Starting 1-methylindole-3-carboxaldehyde ( 1b ), 1- n -butyl-1 H -indole-3-carbaldehyde ( 1e ) [ 60 ], 1-ethyl-1 H -indole-3-carbaldehyde ( 1c ), 1-isopropyl-1 H -indole-3-carbaldehyde ( 1d ) [ 61 ], 1-benzyl-1 H -indole-3-carbaldehyde ( 1f ) [ 62 ], 1-phenyl-1 H -indole-3-carbaldehyde ( 1g ) [ 63 ], 1-acetyl-1 H -indole-3-carbaldehyde ( 1h ) [ 64 ], 1-benzoyl-1 H -indole-3-carbaldehyde ( 1i ) [ 65 ], 1-tosyl-1 H -indole-3-carbaldehyde ( 1j ) [ 66 ], 5-iodo-1 H -indole-3-carbaldehyde ( 1k ) [ 67 ], 5-bromo-1 H -indole-3-carbaldehyde ( 1l ) [ 68 ], 2-phenyl-1 H -indole-3-carbaldehyde ( 1m ) [ 69 ], 2-(4-nitrophenyl)-1 H -indole-3-carbaldehyde ( 1n ) [ 70 ], benzofuran-2-carbaldehyde ( 1p ) [ 71 ], 5-ethylfuran-2-carbaldehyde ( 1s ) [ 72 ], 1-methyl-1 H -pyrrole-2-carbaldehyde ( 1t ) [ 73 ], anthranilamide ( 2a ) [ 74 ], 2-amino-4-chlorobenzamide ( 2b ) [ 75 ], 2-aminobenzohydrazide ( 2e ) [ 76 ], 2-hydroxybenzamide ( 2f ) [ 77 ], 2-amino-5,6-dihydro-4 H -cyclopentathiophene-3-carboxamide ( 2g ) [ 78 ], and 2-amino-2-phenylacetamide ( 2i ) [ 79 ] were synthesized according to known procedures.…”