73424-97-2

Upstream product

• 110994-17-7 S-Ethynyl-N-p-tolyl-thiohydroxylamine 
• 608-05-9 5-methyl-indole-2,3-dione 
• 3484-35-3 5-methylindolin-2-one 

Downstream Products

• 73425-53-3 C-(6-Methyl-2,3,4,9-tetrahydro-thiopyrano[2,3-b]indol-4-yl)-methylamine 

Relevant academic research and scientific papers

One-pot mild and efficient synthesis of [1,3]thiazino[3,2-: A] indol-4-ones and their anti-proliferative activity

A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2-a]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates in situ, which subsequently undergoes intramolecular cyclization to produce indole-fused thiazin-4-ones in good to excellent yields. The cytotoxic screening of the synthesized compounds using MTT assay revealed the anti-proliferative nature of these frameworks against triple negative breast cancer cell lines with the highest activity emanating from 4H-[1,3]thiazino[3,2-a]indol-4-one and 8-methyl-2-propyl-4H-[1,3]thiazino[3,2-a]indol-4-one compounds.

Metal-free hydroamination of alkynes: A mild and concise synthesis of thiazolo[3,2- a ]indoles and their cytotoxic activity

A metal-free, mild and efficient method for the synthesis of thiazolo[3,2- a ]indoles has been developed starting from indoline-2-thiones. The reaction methodology involves first the formation of thermally labile 2-(prop-2-ynylthio)-1 H -indole intermedia

Highly efficient synthesis of thieno[2,3-b]indole derivatives

Thieno[2,3-b]indole derivatives were efficiently prepared via the reaction of 1,3-dihydro-2H-indole-2-thiones with α-bromo-substituted ketones or aldehydes and in the presence of Et3N (Scheme 2 and Table). The reaction took place under very mil

Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: Expanding the scope of the Vilsmeier formylation

(Chemical Equation Presented) Efficient syntheses of the phytoalexins brassilexin, sinalexin, and analogues are demonstrated through the application of the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential formylation-amination of indolin-2-ones is described. Remarkably, this novel aqueous ammonia workup allows the sequential one-pot formylation-amination, expanding substantially the scope of the Vilsmeier formylation of both indoline-2-thiones and indolin-2-ones. The examination of the formylation-amination reaction and optimization of conditions, as well as the syntheses and antifungal activities of several brassilexin analogues, are reported.

Oxindole derivatives

The invention relates to compounds of formula (I), wherein: R2represents hydroxy, halogeno, C1-3alkyl, C1-3alkoxy, C1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro, C2-4alkanoyl, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylthio, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, {overscore (N)}—C1-4alkylcarbamoyl, {overscore (N)},{overscore (N)}-di(C1-4alkyl)carbamoyl, aminosulphonyl, {overscore (N)}—C1-4alkylaminosulphonyl, {overscore (N)},{overscore (N)}-di(C1-4alkyl)aminosulphonyl, C1-4alkylsulphonylamino, or a group R4X1wherein X1represents a direct bond, C2-4alkanoyl, —CONR5R6—, —SO2NR7R8— or —SO2R9— (wherein R5and R7, each independently represents hydrogen or C1-2alkyl and R6, R8and R9each independently represents C1-4alkyl and wherein R4is linked to R6, R8or R9) and R4represents an optionally substituted group selected from phenyl and a 5 or 6-membered heterocyclic group; n is an integer from 0 to 4, R1represents hydrogen, C1-4alkyl, C1-4alkoxymethyl, di(C1-4alkoxy)methyl or C1-4alkanoyl; m is an integer from 0 to 4; and R3represents hydroxy, halogeno, nitro, trifluoromethyl, C1-3alkyl, cyano, amino or R10X2(wherein X2represents a direct bond, —CH2—, or a single or double heteroatom linker group including —S—, —SO— and —NR15— (wherein R15represents hydrogen, C1-3alkyl or C1-3alkoxyC2-3alkyl), and R10is an alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R10is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring. The compounds of formula (I) and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF and FGF, properties of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

A NEW PREPARATION OF N-ARYL-1-ALKYNESULPHENAMIDES AND THEIR THERMAL REARRANGEMENTS INTO INDOLINE-2-THIONES

Reaction of 1-alkynyl-lithio derivatives with N,N-dialkylaminosulphenyl chlorides 3a,b affords the N,N-dialkyl-1-alkynesulphenamides 4.When treated with stoichiometric amounts of a substituted benzenamine and methanesulfonic (or trifluoroacetic) acid, the sulphenamides 4, are converted into N-aryl-1-alkynesulphenamides 6-20.On heating in benzene, many of these sulphenamides 6-20 undergo -sigmatropic rearrangements followed by cyclisation of the intermediate thioketenes yielding the substituted indoline-2-thiones 21-30.