16578-92-0Relevant articles and documents
Biological activity of a small molecule indole analog, 1-[(1H-indol-3-yl)methylene]-2-phenylhydrazine (HMPH), in chronic inflammation
Misra, Chandra Sekhar,Gejjalagere Honnappa, Chethan,Hosur Shrungeswara, Akhila,Unnikrishnan, Mazhuvancherry Kesavan,Jitta, Srinivas Reddy,Daram, Prasanthi,Gourishetti, Karthik,Nayak, Yogendra,Singh, Mahendra Pal
, p. 71 - 83 (2016)
A synthetic small molecule, 1-[(1H-indol-3-yl)methylene]-2-phenylhydrazine (HMPH) was conveniently synthesised by a one-step reaction, purified and characterised by chromatographic and spectroscopic methods. HMPH scavenged free radicals and inhibited lipo
Indole-3-carbaldehydes Arylhydrazones as Multisite C-Nucleophiles in the Reactions with Quinazoline
Azev, Yu. A.,Bakulev, V. A.,Eltsov, O. S.,Ivoilova, A. V.,Koptyaeva, O. S.,Pospelova, T. A.,Seliverstova, E. A.,Tsmokalyuk, A. N.,Yakovleva, Yu. A.
, p. 1601 - 1610 (2020/10/15)
Abstract: C,C-Coupling of indole-3-carbaldehyde arylhydrazones with quinazoline in trifluoroacetic acid has occurred at position 5 or 7′ of the hydrazone molecule and has afforded the σ-adducts. The C,C-coupling has been accompanied by a change in the E-configuration of the C=N bond of the starting hydrazones to the Z-configuration in the formed quinazoline trifluoroacetyl hydrazides.
The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles
Duan, Liancheng,Zhou, Hui,Gu, Yucheng,Gong, Ping,Qin, Mingze
supporting information, p. 16131 - 16137 (2019/11/03)
In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.
