4119-10-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]is used as a potential drug candidate for the development of new medications targeting serotonin receptors. Its interaction with these receptors could be leveraged to address various physiological functions and conditions related to mood regulation and gastrointestinal motility.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2,4(1H,3H)-Quinazolinedione, 3-[2-(1H-indol-3-yl)ethyl]is used as a compound of interest for exploring its pharmacological potential. Further research is necessary to understand its full therapeutic applications and to develop it into effective drugs for treating specific conditions.

Upstream product

• 41470-85-3 2-trichloromethyl-benzo[d][1,3]oxazin-4-one 
• 61-54-1 tryptamine 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 98260-32-3 2-chloro-3-<2-(indol-3-yl)ethyl>-4(3H)-quinazolinone 

Downstream Products

• 84-26-4 rutaecarpine 

Relevant academic research and scientific papers

A SHORT SYNTHESIS OF RUTECARPINE AND/OR VASICOLINONE FROM 2-CHLORO-3-(INDOL-3-YL)ETHYLQUINAZOLIN-4(3H)-ONE: EVIDENCE FOR THE PARTICIPATION OF THE SPIRO INTERMEDIATE

A new route to rutecarpine and/or vasicolinone from 2-chloro-4-quinazolone through an acid catalyzed cyclization of 2-chloro-3-indolylethylquinazolin-4-one has been developed and the mechanism of the cyclization reaction clarified.

ONE POT SYNTHESIS OF QUINAZOLINE DERIVATIVES BY USE OF PALLADIUM CATALYZED CARBONYLATION

One pot synthesis of quinazoline derivatives from a mixture of o-iodoaniline 1a and five membered lactams or N-acyl-o-iodoaniline derivatives, 1b and 1c, and primary amines was effected through the palladium-catalyzed insertion of carbon monoxide.

Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids

Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).