24365-65-9

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 13, p. 144, 1970 DOI: 10.1021/jm00295a041Journal of Heterocyclic Chemistry, 25, p. 789, 1988 DOI: 10.1002/jhet.5570250315

InChI:InChI=1/C9H10N2O/c1-11-6-7-4-2-3-5-8(7)10-9(11)12/h2-5H,6H2,1H3,(H,10,12)

Upstream product

• 4141-08-6 2-Amino-N-methylbenzamid 
• 160354-69-8 2-(methyloxycarbonyl)aminobenzaldehyde 
• 57707-11-6 N-(2-nitrobenzylidene)methanamine 
• 552-89-6 2-nitro-benzaldehyde 
• 56222-08-3 (2-nitrobenzyl)methylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1904-69-4 2-amino-N-methylbenzylamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 117535-91-8 2-amino-N-methylbenzylamine oxalate hydrochloride 
• 57-13-6 urea 

Downstream Products

• 118621-04-8 6-(4-Benzyl-piperazine-1-carbonyl)-3-methyl-3,4-dihydro-1H-quinazolin-2-one; hydrochloride 
• 118621-00-4 3,4-dihydro-3-methyl-6-<4-(4-oxo-4-phenylbutyl)-1-piperazinylcarbonyl>-2(1H)-quinazolinone hydrochloride 
• 328956-25-8 1-benzyl-6-bromo-3-methyl-3,4-dihydroquinazolin-2(1H)-one 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Provided herein are novel heterocyclic compounds, for example, compounds having Formula I, I-P, II, lI-P, or III. Also provided herein are pharmaceutical compositions comprising the compounds and methods of using the same, for example, in inhibiting aldehyde dehydrogenases and/or for treating various cancers, cancer metastasis, type 2 diabetes, pulmonary arterial hypertension (PAH) or neointimal hyperplasia (NIH).

Synthesis of substituted 3,4-dihydroquinazolinonesviaa metal free Leuckart-Wallach type reaction

The 3,4-dihydroquinazolinone (DHQ) moiety is a highly valued scaffold in medicinal chemistry due to the vast number of biologically-active compounds based on this core structure. Current synthetic methods to access these compounds are limited in terms of diversity and flexibility and often require the use of toxic reagents or expensive transition-metal catalysts. Herein, we describe the discovery and development of a novel cascade cyclization/Leuckart-Wallach type strategy to prepare substituted DHQs in a modular and efficient process using readily-available starting materials. Notably, the reaction requires only the addition of formic acid or acetic acid/formic acid and produces H2O, CO2and methanol as the sole reaction byproducts. Overall, the reaction provides an attractive entry point into this important class of compounds and could even be extended to isotopic labellingviathe site-selective incorporation of a deuterium atom.

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A Convenient Preparation of 3-Methyl-3,4-dihydro-2(1H)-quinazolinone

3-Methyl-3,4-dihydro-2(1H)-quinazolinone (5) can be prepared in good yield and quality from o-nitrobenzyl chloride (1).The three-step sequence requires no purification of intermediates or final product.

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A method for increasing cardiotonic contractility in humans or other animals using a class of benzodiazinonepryidazinone and hydroxy-pyrazolyl compounds and pharmaceutical compositions including the same.