91182-56-8Relevant academic research and scientific papers
Synthesis, characterization and molecular structures of homologated analogs of 2-bromo-3-(n-alkylamino)-1,4-napthoquinone
Salunke-Gawali, Sunita,Pawar, Omkar,Nikalje, Milind,Patil, Rishikesh,Weyhermüller, Thomas,Puranik, Vedavati G.,Badireenath Konkimalla
, p. 97 - 103 (2014)
Four analogues of 2-bromo-3-(n-alkylamino)-1,4-napthoquinone (where n-alkyl is methyl in L-1Br, ethyl in L-2Br, propyl in L-3Br and butyl in L-4Br) are synthesized and characterized. A reaction mechanism is proposed for the formation of L-1Br to L-4Br from the starting material 2,3-dibromo-1,4- naphthoquinone. The νNH frequency in the FT-IR spectra is affected by the intramolecular hydrogen bonding in L-1Br to L-4Br and is observed 3267 cm-1 in L-2Br. A shift of 25 cm-1 is observed in the νCBr frequency in all the compounds as compared to 2,3-dibromo-1,4-naphthoquinone (627 cm-1). A broad charge transfer band is observed between 400 and 600 nm in the UV-Vis spectra, which imparts red colour to all the compounds. Molecular structures of L-2Br and L-3Br were studied by single crystal X-ray diffraction studies. Molecules of L-2Br crystallize in Pca21, whereas the molecule L-3Br crystallizes in the P-1 space group. Molecules of L-2Br forms a polymeric chain through NHa?O interaction and forms beautiful butterfly like arrangement of molecules when viewed down the 'a' axis. Ladder like polymeric chain of molecules is observed in L-3Br via CHa?O and NHa?O interactions. Every alternating neighbouring chains of L-3Br, show stacking interactions between the quinonoid rings of the molecules, however this interaction is not observed in L-2Br.
Oxidative free radical reactions between 2-amino-1,4-naphthoquinones and carbonyl compounds
Wu, Yi-Lung,Chuang, Che-Ping,Lin, Pi-Yun
, p. 5543 - 5549 (2001)
The manganese(III) initiated oxidative free radical reaction provides a novel method for the synthesis of benzo[f]indole-4,9-diones from 2-amino-1,4-naphthoquinones and carbonyl compounds. The regioselectivity of this reaction was also studied with unsymmetrical ketones from which both isomeric indoles 10 and 11 were formed. With α-halo, α-phenoxy and α-methanesulfonyl ketones, in most cases, this reaction gave high regioselectivity. With 2-alkyl substituted-1,3-dione 14, indole 11 was obtained as the only product.
Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C?H Halogenation
Dalai, Pallaba Ganjan,Palit, Kuntal,Panda, Niranjan
supporting information, p. 1031 - 1038 (2022/02/02)
A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C?H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur
The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors
Valente, Claudia,Moreira, Rui,Guedes, Rita C.,Iley, Jim,Jaffar, Mohammed,Douglas, Kenneth T.
, p. 5340 - 5350 (2008/03/14)
A series of 1,4-naphthoquinone derivatives diversely substituted at C-2, C-3, C-5 and C-8, prepared by reaction of amines, amino acids and alcohols with commercial 1,4-naphthoquinones, has been evaluated against papain and bovine spleen cathepsin B. These
One-step synthesis of 1,2,3,4-tetrahydrobenzo[g]quinazoline-5,10-dione derivatives from vitamin K3
Ohta,Hinata,Yamashita,Kawasaki,Jinda,Horie
, p. 1730 - 1735 (2007/10/02)
The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1,4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1,3-Dialkyl-1,2,3,4-tetrahydrobenzo[g]quinazoline-5,10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.
