6789-51-1Relevant articles and documents
A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination
Tang, Yu,Yu, Biao
, (2022/03/27)
A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.
MALEIMIDE DERIVATIVES AS MODULATORS OF WNT PATHWAY
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Paragraph 0162; 0163; 0164; 0165, (2015/07/07)
The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, or a pharmaceutically acceptable salt, solvate or polymorph therof, including all tautomers and stereoisomers thereof wherein R1represents optionally substituted alkyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkoxy); optionally substituted carbocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6alkoxy, C1-6haloalkyl, C1-6haloalkoxy and halo); or -alkylaryl; R2 represents H; or alkyl; R3 represents H; or alkyl; U, V and W represent -(CH2)-; or U and V together represent -CH=CH- and W represents C=O; Y represents aryl; heteroaryl; optionally substituted carbocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6alkoxy, C1-6haloalkyl, C1-6haloalkoxy and halo); or optionally substituted heterocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6 alkoxy, -C(O)OC1-6alkyl, -C(O)C1-6alkyl and-C(O)NHC1-6alkyl); and Z represents aryl; heteroaryl; optionally substituted carbocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6alkoxy, C1- 6haloalkyl, C1-6haloalkoxy and halo); or optionally substituted heterocyclyl (wherein optional substituents include one or more substituents each independently selected from C1-6alkyl, C1-6. alkoxy, -C(O)OC1-6alkyl, -C(O)C1-6alkyl and -C(O)NHC1-6alkyl).
An Unusual Ring Contraction of 7-Methyl-1,7-naphthyridinium and 6-Methyl-1,6-naphthyridinium Salts in Reaction with Liquid Ammonia/Potassium Permanganate
Wozniak, M.,Plas, H. C. van der,Harkema, S.
, p. 3435 - 3437 (2007/10/02)
Treatment of 7-methyl-1,7-naphthyridinium iodide (1) with liquid ammonia/potassium permanganate gives the 8-imino compound 3 and two ring contraction products, which by 1H NMR spectroscopy were assigned as 3-amino-1,3-dihydro-2-methyl-4-azaisoindol-1-one (5) and 1,3-dihydro-2-methyl-4-azaisoindole-1,3-dione (6).The structure of 5 was confirmed by X-ray analysis.Similarly from 6-methyl-1,6-naphthyridinium iodide (2) the 5-imino compound 7 together with 1-amino-1,3-dihydro- (8) and 1-imino-1,3-dihydro-2-methyl-4-azaisoindol-3-one (9) were formed. 1H NMR spectroscopy unequivocally shows that 1 and 2 are converted with ammonia into 8-amino-7,8-dihydro-7-methyl-1,7-naphthyridine (11) and 5-amino-5,6-dihydro-6-methyl-1,6-naphthyridine (12), respectively.The mechanism of the ring contraction is discussed.
