32725-30-7

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 19, p. 1117, 1982 DOI: 10.1002/jhet.5570190527

Upstream product

• 121568-13-6 1-(2-fluorobenzoyl)-2-methylthio-2-imidazoline 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 344312-25-0 2-ethoxythiocarbonylamino-benzoic acid methyl ester 
• 107-15-3 ethylenediamine 
• 853995-64-9 methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthranilate 
• 20112-79-2 2-methylthioimidazoline 
• 118-48-9 isatoic anhydride 
• 118-92-3 anthranilic acid 
• 18741-24-7 3-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 727-62-8 2-chloro-3-phenylquinazoline-4-(3H)-one 
• 27631-28-3 2,3-dihydroimidazo[1,2-c]quinazolin-5-amine 
• 552-89-6 2-nitro-benzaldehyde 
• 1361234-34-5 methyl N-cyano-2-nitrobenzenecarboximidoate 
• 1227479-37-9 N-(2-azidoethyl)-N-cyanobenzamide 

Downstream Products

• 1019197-20-6 BrH*C₂₆H₃₁N₃O₃ 
• 1019197-22-8 C₁₈H₁₅N₃O₂ 
• 1019197-18-2 C₁₈H₁₅N₃O₂ 
• 1019197-19-3 BrH*C₁₈H₁₄ClN₃O₂ 
• 40534-69-8 10-(4-chloro-benzyl)-2,10-dihydro-3H-imidazo[2,1-b]quinazolin-5-one 

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).

Synthesis of 2,4-diaminoquinazolines and tricyclic quinazolines by cascade reductive cyclization of methyl N -cyano-2-nitrobenzimidates

An efficient route to N4-substituted 2,4-diaminoquinazolines has been developed by employing tandem condensation of cyanoimidate-amine and reductive cyclization in iron-HCl system. This method is tolerant of a following intramolecular N-alkylation and produces two fused heterocycles in a one-pot procedure. This protocol is a facile two-step synthesis of tricyclic quinazolines, which is effected by potent cyanoimidation and tandem reductive cyclization from 2-nitrobenzaldehydes. Moreover, the forming process of tricyclic quinazolines has been investigated from the ring-opening/ring-closing cascade point of view. It is found that the preparation of tricyclic quinazolinones in good yields relies on the selective hydrolysis of tricyclic quinazolines in base or acid system.

Radical synthesis of guanidines from N-Acyl cyanamides

Chemical Equation Presented Center stage: Additions of nitrogen-centered radicals to cyanamide compounds provided the first radical synthesis of aromatic polycyclic guanidine derivatives (see scheme). Modular assembly of the substrates allows for a rapid increase of the molecular complexity of scaffolds, which have potential applications for medicinal chemistry.

Mechanism of the reaction of neutral and anionic N-nucleophiles with α-halocarbonyl compounds

N-Acylalkylation of neutral and anionic N-nucleophiles with α-halocarbonyl compounds was investigated by quantum chemical methods in terms of the density functional theory and by experimental methods for 2,3-dihydroimidazo[2,1-b]quinazolin-1(10)H-5-one, its N-anion, and simpler model structures. High reactivity of these reagents is determined primarily by stabilization of transition states (TS) by bridge bonds involving halogen or nitrogen atoms rather than by conjugation, as has been commonly accepted. Bridged TS are formed by both the substitution mechanism S N 2 and the addition-elimination mechanism. α-Haloalkyl-substituted zwitterions, which are potential intermediates of stepwise N-acylalkylation of neutral N-nucleophiles, do not exist in the isolated state, but they are rather efficiently stabilized upon solvation. These zwitterions, as well as analogous O-anions generated from anionic N-nucleophiles, can serve as intermediates of N-acylalkylation, as was demonstrated by localization of the corresponding TS.

Synthesis of novel 2,3-substituted quinazolin-4-ones by condensation of alkyl or aromatic diamines with 5-(N-arylimino)-4-chloro-5H-1,2,3-dithiazoles

The work described in this paper is a further example of the utility of Appel's salt in the conception of novel heterocyclic rings. We confirmed that primary alkyldiamines may react easily with the methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthrani

A rapid and convenient synthesis of novel 1-imino-2,3-dihydro-1H- pyrazino[2,1,-b]quinazolin-5-ones

Exploring original approaches for the synthesis of therapeutic agents having a quinazoline part, we discovered that novel 3,4-dihydro-2H-pyrazino[2,1, -b]quinazolines (3) may be rapidly and easily obtained via the chemistry of 4,5-dichloro-1,2,3-dithiazol

Preparation of Imidazoquinazolin-5(3H)-ones and Related Tricyclic Systems Using a Novel, Double Displacement Reaction

New methodology is described for the construction of tricyclic heterocycles.Thus, a double displacement reaction of 1-(2-fluorobenzoyl)-2-methylthio-2-imidazoline (8a) with 1,1-dialkylhydrazines gave 10-substituted 2,10-dihydroimidazoquinazolin-5(3H)-ones in good yield.The corresponding 1-(2-nitrobenzoyl)-2-methylthio-2-imidazolines also underwent double displacement reactiones with hydrazines.Other tricyclics made using double displacement reactions were pyrimidoquinazolines, imidazopyridopyrimidines, and imidazopyrazolopyrimidines.Treatment of 8a with hydrazine hydrate or methylhydrazine gave products resulting from displacement, but did not afford fused benzotriazepinones.

Synthesis of 4(3H)-Quinazolinones from Derivatives of Methyl 2-Isothiocyanatobenzoate

Ethyl N-((2-methoxycarbonylphenyl)thiocarbamate (2), N-(2-ethoxycarbonylphenyl)-4-methoxythiobenzamide (3b), and 2-(4-methoxyphenyl)4H,-3,1-benzothiazin-4-one (4a), react with nucleophilic reagents containing at least one primary amino group to yield a variety of 2-substituted and 2,4-disubstituted 4(3H)-quinazolinones, as well as some tricyclic and tetracyclic products.