22458-10-2

Upstream product

• 1253935-40-8 C₁₁H₁₂N₄O 
• 860193-39-1 3-(3-iodopropyl)-3H-quinazolin-4-one 

Downstream Products

• 133566-53-7 1-benzoyl-1,2-dihydrodeoxyvasicinone 
• 1097058-70-2 1-(o-chlorophenylcarbamoyl)-1,2-dihydrodeoxyvasicinone 
• 1097058-69-9 1-(o-nitrophenylcarbamoyl)-1,2-dihydrodeoxyvasicinone 
• 1097058-66-6 1-(p-methylbenzoyl)-1,2-dihydrodeoxyvasicinone 
• 1097058-74-6 1-(p-methylphenylcarbamoyl)-1,2-dihydrodeoxyvasicinone 
• 1097058-65-5 1-(p-nitrobenzoyl)-1,2-dihydrodeoxyvasicinone 
• 1097058-72-4 1-(m-chlorophenylcarbamoyl)-1,2-dihydrodeoxyvasicinone 

Relevant academic research and scientific papers

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.

Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin

Alkyl, aryl, heteroaryl and acyl radicals have been cyclised onto the 2-position of 3H-quinazolin-4-one. The side chains containing the radical precursors were attached to the nitrogen atom in the 3-position. The cyclisations take place by aromatic homolytic substitution hence retain the aromaticity of the 3H-quinazolin-4-one ring. The highest yields were obtained using hexamethylditin to facilitate cyclisation rather than reduction without cyclisation. The alkaloids deoxyvasicinone 2, mackinazolinone 3, tryptanthrin 4, luotonin A 5 and rutaecarpine 8 were synthesised by radical cyclisation onto 3H-quinazolin-4-one. This journal is The Royal Society of Chemistry.