Synthesis of Substituted Dibenz-oxazepines and Dibenzthiazepine Using of 4-Bromo-5-nitrophthalonitrile

Abstract

Proposed a method of synthesis of new cyano containing compounds of oxazepine and thiazepine series based on activated aromatic nucleophilic substitution reaction of bromine atom and nitro group in 4-bromo-5nitrophthalonitrile by various bifunctional O-, N-, S-nucleophiles.

New Nitrogen-Containing Five-Membered Heterocyclic ortho-Dicarbonitriles for Preparation of Macroheterocycles

“…Despite the progress made recently in this field, alternative methods of synthesizing these compounds continue to be developed. First of all, it should be noted that S N Ar-reactions occurring with the participation of 4-nitro-and 4-bromo-5-nitrophthalonitrile under homo-and hetero-conditions allow the study of the synthesis of a large number of diverse aromatic and heterocyclic compounds, [17][18][19][20][21][22][23] and related compounds that are condensed with the phthalonitrile fragment (Scheme1). In addition, we have developed methods for the synthesis of 3-substituted 2-amino-1-hydroxy-1H-indole-5,6-dicarbonitriles (2), [24] and 2-aryl-1-Hydroxy-1H-indole-5,6-dicarbonitriles (3), [25] based on 4-bromo-5-nitrophthalonitrile (1) (Scheme 2).…”

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines by Two Tandem SNAr Events. Part 2 – The Use of o‐[N‐(Hetero)aryl]aminomethyl Phenols

“…While some degree of delocalization of the negative charge in 4 is probably needed to enable formation of the latter, replacing the carbonyl substituent in 1f with a (hetero)aromatic substituent ( 9 ) may serve the purpose and favor the Smiles rearrangement for those substrates 2 which previously did not yield [1.4]oxazepines 8 (Figure ). Herein, we present the outcome of testing this hypothesis …”

Preparation of benzoannulated seven- and eight-membered heterocycles from 2,4,6-trinitrobenzoyl chloride

“…In this work aimed at the utilization of aromatic polynitro compounds, we found that cyclization of ortho-nitrobenzoic acid 2-hydroxyanilides afforded dibenz[b,f] [1,4]oxazepin-11(10H)-ones. 6,7 We demonstrated that intramolecular nucleophilic displacement of a nitro group in 2,4,6-trinitrobenzoic acid amides A is a general method of preparing benzoannulated seven-and eightmembered N-containing heterocycles B (Scheme 1).…”