74897-46-4

Usage

Derivative of indole

contains a carbonitrile group (CN) and an amino group (NH2)

Substitution

sulfonamide group (SO2NH2) linked to a 4-methylphenyl moiety (C6H4CH3)

Usage

in pharmaceutical research and drug development due to potential pharmacological properties

Applications

as a building block in the synthesis of organic compounds and in medicinal chemistry.

Upstream product

• 23300-99-4 1-tosyl-1H-indazole 
• 107-14-2 chloroacetonitrile 
• 1591-37-3 2-amino-6-methoxybenzonitrile 
• 31659-28-6 N-(2-Cyanophenyl)-4-methylbenzenesulfonamide 

Downstream Products

• 1227096-68-5 3-(p-tosylamino)indole-2-carbonitrile 
• 1192690-93-9 3-amino-1H-indole-2-carbonitrile 
• 1227096-71-0 3-(benzenesulfonylamino)indole-2-carbonitrile 

Relevant academic research and scientific papers

Direct N-Alkylation and Kemp Elimination Reactions of 1-Sulfonyl-1H-Indazoles

The reactions of 1-sulfonyl-1H-indazoles under basic conditions are discussed, and the direct N-alkylation and Kemp elimination reactions of these compounds are reported. A series of 2-(p-tosylamino)benzonitriles and N-alkyl indazoles were prepared in good yields. Moreover, the 2-(p-tosylamino)benzonitriles could be transformed into a diverse range of important derivatives in a one-pot reaction. This method was successfully applied to the total syntheses of quindolinone and cryptolepinone; quindolinone was prepared in a one-pot reaction from 1-sulfonyl-1H-indazole.

Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol

Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4→5) and the reductive detosylation (4→2) are proposed. All new compounds are fully characterised.

Substituted 5H-pyrimido[5,4-b]indoles

Substituted 5H-pyrimido[5,4-b]indoles of Formula I STR1 wherein R 2 is halogen; the oxadiazolyl group STR2 wherein R"" is lower alkyl with up to 3 carbon atoms; C 1-5 -alkyl, cycloalkyl, aralkyl, or aryl; OR I, SO n R I with n being 0, 1, or 2, or STR3 wherein R I is hydrogen, C 1-5 -alkyl, cycloalkyl, aralkyl, or aryl; STR4 wherein R II and R III are hydrogen, C 1-5 -alkyl, C 3-5 -alkenyl, cycloalkyl, aralkyl, aryl, or, with the connecting N-atom, a 5- or 6-membered heterocyclic ring; andR A is hydrogen; the oxadiazolyl group STR5 wherein R"" is lower alkyl with up to 3 carbon atoms; halogen, nitro, OR I, SO n R I with n being 0, 1, or 2, STR6 wherein R I is hydrogen, C 1-5 -alkyl, cycloalkyl, aralkyl, or aryl; STR7 wherein R II and R III are hydrogen, C 1-5 -alkyl, cycloalkyl, C 3-5 -alkenyl, aralkyl, aryl, or, with the connecting N-atom, a 5- or 6-membered heterocyclic ring; orPO(OR) 2wherein R is C 1-5 -alkyl, exhibit strong affinity for binding to benzodiazepine receptors.The novel compounds are suitable for use in psychopharmaceutical preparations.

Tricyclic Systems Obtained from Some 3-Aminobenzothiophen Derivatives

4-Hydroxybenzothienopyridin-2(1H)-one (3) was obtained by cyclisation of a benzothiophen derivative containing either 2-CO2Et, 3-NH.CO.CH2.CO2Et or 2-CO.CH2.CO2Et, 3-NH2 substituents. 3-Amino-2-formyl-, 3-amino-2-acetyl-, and 3-amino-2-acetyl-5-nitro-benzothiophens were converted into the corresponding 3-thiocyanato-compounds, which gave tricyclic systems when treated with hydroxylamine.Heating these with polyphosphoric acid gave benzothienoisothiazole, and its 3-methyl and 3-methyl-7-nitro-derivatives respectively.Nitration, formylation, and oxidation reactions of 3-methylbenzothienoisothiazole have been investigated.