19050-63-6

Upstream product

• 10328-92-4 N-Methylisatoic anhydride 
• 64-04-0 phenethylamine 
• 118-48-9 isatoic anhydride 
• 13061-96-6 dihydroxy-methyl-borane 
• 19050-62-5 N-(2-phenylethyl)-2-aminobenzamide 

Downstream Products

• 75652-62-9 1-methyl-3-(2'-phenylethyl)-1H,3H-quinazoline-2,4-dione 
• 55854-99-4 1-methyl-3-phenethyl-2,3-dihydroquinazolin-4(1H)-one 
• 19007-58-0 N-[2-(3,4-dihydro-isoquinolin-1-yl)-phenyl]-N-methyl-toluene-4-sulfonamide 
• 200404-31-5 N-Methyl-2-(p-toluolsulfonylamino)-benzoesaeure-(2-phenylethyl)-amid 

Relevant academic research and scientific papers

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.

Syntheses of quinazoline-2,4-dione alkaloids and analogues from Mexican Zanthoxylum species

Quinazolinone and quinazolinedione derivatives are of considerable interest due to their wide array of pharmacological properties. In this paper we report the synthesis of ten quinazolinediones. The previous isolation of two of these compounds, namely 1-methyl-3-(2′-phenylethyl)-1H,3H-quinazoline-2,4-dione and 1-methyl-3-[2′-(4′-methoxyphenyl)ethyl]-1H,3H-quinazoline-2,4- dione, from the seed husks of Mexican Zanthoxylum species has been reported.

Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution

1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3, 4-tetrahydroisoquinolines were obtained in optically pure form (>99% ee).

A new scavenger resin for amines

Isatoic anhydride (1) can be attached to Merrifield resin by alkylation on its nitrogen. A maximum loading of 3.2 mmol of anhydride/g of 5 was achieved. This resin, due to the highly reactive anhydride moiety, completely removes primary and secondary aliphatic amines from reactions where they are used in excess.