53645-79-7

Upstream product

• 106-31-0 butanoic acid anhydride 
• 59026-76-5 5-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidinium iodide 
• 124-13-0 Octanal 
• 110212-00-5 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carbonitrile 
• 108-24-7 acetic anhydride 
• 104-87-0 4-methyl-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 630-19-3 pivalaldehyde 
• 123-62-6 propionic acid anhydride 
• 529-20-4 2-methylphenyl aldehyde 
• 5334-48-5 4-chloro-1-(phenyl)-1H-pyrazolo[3,4-d]pyrimidine 
• 78-94-4 methyl vinyl ketone 
• 67-64-1 acetone 

Downstream Products

• 98512-46-0 4-(1-phenyl-1H-pyrazolo<3,4-d>pyrimidin-4-yl)quinazoline 
• 4252-31-7 N-formylbenzamide 
• 62564-91-4 5-amino-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 14246-94-7 4-anilino-5-pyrimidinecarbonitrile 
• 110212-00-5 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4-carbonitrile 
• 116943-89-6 5-(4-Methoxy-benzoyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 
• 116943-90-9 5-(4-Nitro-benzoyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 
• 116943-86-3 5-Acetyl-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 
• 116943-87-4 5-Benzenesulfonyl-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 
• 110212-03-8 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetamide 
• 110212-04-9 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetate 
• 110212-01-6 α,1-diphenyl-1H-pyrazolo<3,4-d>pyrimidin-4-ylmethyl benzoate 
• 65143-08-0 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile 
• 59563-52-9 4,4'-bis<1-phenyl-1H-pyrazolo<3,4-d>pyrimidine> 

Relevant academic research and scientific papers

Indium-mediated dehalogenation of haloheteroaromatics in water

It turned out that indium metal was applicable to the dehalogenation of aromatic halides in water. This method is facile and safe compared with the conventional methods such as Pd-C, Raney Ni, or halogen-metal exchange.

The tellurium-lithium exchange reaction: Selective functionalization of electron-deficient heteroaromatics

Electron-deficient heteroaromatic tellurides, which was obtained from the corresponding haloheteroaromatics, reacted selectively with n-butyllithium to give the lithio derivatives.

A tandem decarboxylation/Diels-Alder reaction of 5-amino-1-phenyl-4-pyrazolecarboxylic acid with 1,3,5-triazines

A tandem decarboxylation/Diels-Alder reaction of 5-amino-1-phenyl-4-pyrazolecarboxylic acid with various 1,3,5-triazines was reported. The dienophile, 5-amino-1-phenylpyrazole, was generated in situ via decarboxylation and immediately trapped by 1,3,5-triazines leading to 4,6-disubstituted 1-phenylpyrazolo[3,4-d]pyrimidines in one step.

The selective deiodination of iodoheterocycles using the PhSiH3 - In(OAc)3 system

Nitrogen-containing π-deficient heterocyclic iodides such as iodoquinolines or iodopyridines were deiodinated by treatment with phenylsilane catalyzed by indium acetate to give the corresponding deiodinated heterocycles at ambient temperature.

Chemistry of heteroaryltriphenylphosphonium iodides: Preparation from iodoheteroaromatics and elimination of the phosphonium iodide group using basic solvents

α- and γ-Iodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields, β-lodoheteroaromatics, which are less reactive with triphenylphosphine compared to α- or γ-compounds, were con

Dehalogenation and barbier-type hydroxyalkylation of π-deficient haloheterocycles using indium

The reaction of π-deficient haloheterocycles with indium metal in water gave corresponding dehalogenated heterocycles. The use of diluted hydrochloric acid instead of water accelerated the reductive reactivity of indium metal. Furthermore, Barbier-type additions proceeded by reactions of α-iodoheterocycles with indium in the presence of pivalaldehyde.

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.

Studies on Pyrazolopyrimidine Derivatives. XV. Reactions Involving the Formation of the Anion of the Reissert Compound Derived form 1H-Pyrazolopyrimidine

The anion (A) of the Reissert compound (1, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile) was found to react with electrophiles in two ways.One is nucleophilic attack of the anion A.The other is self-decomposition of the anion A.Thus, A underwent nucleophilic attack with aromatic and aliphatic aldehydes (4a-j), resulting in the formation of the corresponding α-aryl (or alkyl)-1-phenyl-1H-pyrazolopyrimidin-4-ylmethyl benzoates (6a-j) together with 1-phenyl-1H-pyrazolopyrimidine (2), the 4,4'-dimer (7) of 2, O-benzoylaroins (8a-d), and O-benzoylcyanohydrins (9e-j).Nucleophilic substitution took place in the reaction of A with 2,4-dinitrochlorobenzene (14a) and methyl iodide (14d), giving the 4-(2,4-dinitrophenyl) derivative (17a) of 2 and 5,7-dibenzoyl-4-methyl-1-phenyl-4-(1-phenyl-1H-pyrazolopyrimidin-4-yl)-4,5,6,7-tetrahydro-1H-pyrazolopyrimidine-6-carbonitrile (19), respectively.However, the anion A did not react with other aryl (or alkyl) halides (14b, c, e), ketones (11a, b), 2-alkenonitriles (21a, b), and dimethylacetylenedicarboxylate (22), and underwent the known self-decomposition, resulting in the formation of products such as 2, 7, the cyano derivative (18) of 2, and the ester 6a.Keywords - pyrazolopyrimidine; Reissert compound; aldehyde; aryl halide; nucleophilic attack; self-decomposition; pyrazolopyrimidinemethanol

Studies on Pyrazolopyrimidine Derivatives. XIV. Preparation and Reactions of 1-Phenyl-1H-pyrazolo-pyrimidine Reissert Compound

The Reissert reaction of 1-phenyl-1H-pyrazolopyrimidine (4) in anhydrous methylene chloride using benzoyl chloride, trimethylsilyl cyanide, and a catalytic amount of aluminium chloride gave the corresponding Reissert compound (3, 5-benzoyl-4,5-dihydro-1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile) in 95percent yield.The alkaline hydrolysis of 3 in methanol resulted in the formation of 4, benzoic acid (7), and the 4,4'-dimer (9) of (4).The acid hydrolysis in dimethyl sulfoxide and in methanol proceeded with ring fission to give 5-amino-α-benzamido-1-phenyl-1H-pyrazole-4-acetonitrile (13), the acetamide (14), and the acetate (15).Compound 3 reacted with sodium hydride in dimethylformamide to give 4, 9, 1-phenyl-1H-pyrazolopyrimidine-4-carbonitrile (20), α,1-diphenyl-1H-pyrazolopyrimidin-4-ylmethyl benzoate (21), and O-benzoylmandelonitrile (22).In the present paper, we compare the chemical properties of 3 with those of the isoquinoline Reissert compound (1, 2-benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile).Keywords-pyrazolopyrimidine Reissert compound; preparation; chemical property; hydrolysis; pyrazoleacetonitrile; carbanion; rearrangement; pyrazolopyrimidinemethanol

Transformation of Quinazoline into 2(1H)-Quinolinones with Alkanoic Anhydrides

Quinazoline (1) was transformed into 3-substituted 2(1H)-quinolinones (4) by reaction with alkanoic anhydrides (3).Similar transformation was also found to occur with 5-methyl-1-phenyl-1H-pyrazolopyrimidinium iodide (9), giving 5-substituted 1-phenyl-1H-pyrazolo-pyridine-6-yl alkanoates (10).Keywords-quinazoline; quinolinone; alkanoic anhydride; ring transformation; pyrazolo-pyrimidinium salt; pyrazolopyridine