Interaction of 3‐(2‐Aminophenyl)‐6‐R¹‐1,2,4‐triazin‐5‐ones with Acylating Reagents: An Efficient Method for Preparation of 6‐Substituted 3‐R¹‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐ones

Abstract

The series of 6‐substituted 3‐R1‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐one was prepared via condensation of 3‐(2‐aminophenyl)‐6‐R1‐1,2,4‐triazin‐5‐ones with acylating reagents. Particularities of 1H NMR spectra have been also discussed based on the comparison of experimental and theoretical results for 3‐methyl‐6‐phenyl‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐one and its 4,3‐isomer.

Synthesis of 6-chloro(dichloro-, trichloro-)-methyl-3-R-6,7-dihydro-2H-[1,2,4]triazino[2,3-c]- quinazolin-2-ones and their modification in reactions with nucleophilic and non-nucleophilic bases

“…Listed above processes have the disadvantages including the usage of toxic reagents and low regioselectivity. Cyclocondensation of NÑÑÑN-nucleophiles with halogen-containing reagents (halogen-substituted aldehydes, halogen-substituted acids and their derivatives) can be considered as a promising alternative approach for the synthesis of heterocyclic compounds with halogen-substituted alkyl fragments [2,3]. These methods have undeniable advantages when possibility of variation of halogen atoms quantity and saturation state of the cycle are required.…”

Tandem heterocyclization of 2‐(azolyl‐(azinyl‐))anilines as an efficient method for preparation of substituted pyrrolo[1,2‐a]azolo‐(azino‐)[c]quinazolines

“…The structures of heterocycles resulting from modification of the abovementioned initial compounds depend on the nature of electrophilic reagents as well as on the reaction conditions. Thus, compounds 1‐3 in [5 + 1]‐cyclocondensation with acylating agents yielded aromatic tricyclic systems . In the same time, the reaction of compounds 1‐3 with ethyl chloroformate, N , N ′‐carbonyldiimidazol, carbon disulfide, and sodium (potassium) O‐methyl carbonodithioates yielded dihydroazolo‐(azino‐)[ c ]quinazoline‐ones(thiones) .…”