22458-52-2

Upstream product

• 2059-76-9 4-iodophenyl isothiocyanate 
• 118-92-3 anthranilic acid 

Downstream Products

• 77066-38-7 [4-(4-Iodo-phenyl)-5-oxo-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-1-yl]-acetic acid ethyl ester 
• 77066-33-2 1-Hydroxy-4-(4-iodo-phenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77747-31-0 1-n-Butyl-4-(p-iodphenyl)-s-triazolo<4,3-a>chinazol-5-on 
• 77747-27-4 4-(4-Iodo-phenyl)-1-mercapto-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 77747-24-1 4-(4-Iodo-phenyl)-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one 
• 68357-89-1 2-Hydrazino-3-p-iodphenylchinazol-4-on 

Relevant academic research and scientific papers

Divergent 2-Chloroquinazolin-4(3H)-one Rearrangement: Twisted-Cyclic Guanidine Formation or Ring-Fused N-Acylguanidines via a Domino Process

A highly efficient 2-chloroquinazolin-4(3H)-one rearrangement was developed that predictably generates either twisted-cyclic or ring-fused guanidines in a single operation, depending on the presence of a primary versus secondary amine in the accompanying diamine reagent. Exclusive formation of twisted-cyclic guanidines results from pairing 2-chloroquinazolinones with secondary diamines. Use of primary amine-containing diamines permits a domino quinazolinone rearrangement/intramolecular cyclization, gated through (E)-twisted-cyclic guanidines, to afford ring-fused N-acylguanidines. This scalable, structurally tolerant transformation generated 55 guanidines and delivered twisted-cyclic guanidines with robust plasma stability and an abbreviated total synthesis of an antitumor ring-fused guanidine (4 steps, 55 % yield).