74763-71-6

Upstream product

• 618-40-6 1-Methyl-1-phenylhydrazine 
• 937-23-5 4-bromo-N-nitroso-N-methylaniline 
• 589-21-9 (4-bromophenyl)hydrazine 
• 74-88-4 methyl iodide 
• 106-40-1 4-bromo-aniline 
• 100-61-8 N-methylaniline 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 6911-87-1 4-bromo-N-methylaniline 
• 7647-01-0 hydrogenchloride 
• 7726-95-6 bromine 
• 18804-73-4 1-[(4-Bromo-phenyl)-hydrazono]-propan-2-one 

Downstream Products

• 114202-80-1 D-arabino-[2]hexosulose-bis-[(4-bromo-phenyl)-methyl-hydrazone] 
• 86809-04-3 5-[(4-Bromo-phenyl)-methyl-hydrazono]-6,6,6-trifluoro-2,2-dimethyl-hexan-3-one 
• 76051-09-7 methyl 2--4-phenyl-4-oxobutyrate 
• 80588-71-2 2-[(4-Bromo-phenyl)-methyl-hydrazono]-succinic acid diethyl ester 
• 74763-65-8 1,4-Bis(p-bromophenyl)-1,4-dimethyl-2-tetrazene 
• 6911-87-1 4-bromo-N-methylaniline 
• 112554-51-5 O⁴-β-D-galactopyranosyl-D-arabino-[2]hexosulose-1-[(4-bromo-phenyl)-methyl-hydrazone]-2-thiosemicarbazone 
• 69918-17-8 6-bromo-3-phenylbenzo[e][1,2,4]triazine 
• 924645-57-8 5-bromo-1-methyl-3-phenyl-1H-indazole 
• 848749-78-0 5-bromo-1,3-dimethyl-2-phenyl-1H-indole 
• 111272-46-9 O⁴-β-D-galactopyranosyl-D-arabino-[2]hexosulose-1-[(4-bromo-phenyl)-methyl-hydrazone] 

Relevant academic research and scientific papers

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Rh(iii)-catalyzed, hydrazine-directed C-H functionalization with 1-alkynylcyclobutanols: A new strategy for 1: H -indazoles

Rh(iii)-catalyzed coupling of phenylhydrazines with 1-alkynylcyclobutanols was realized through a hydrazine-directed C-H functionalization pathway. This [4+1] annulation, based on the cleavage of a Csp-Csp triple bond in alkynylcyclobutanol, provides a new pathway to prepare diverse 1H-indazoles under mild reaction conditions. This journal is

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

Discovery and structure-activity relationships of phenyl benzenesulfonylhydrazides as novel indoleamine 2,3-dioxygenase inhibitors

A novel class of phenyl benzenesulfonylhydrazides has been identified as potent inhibitors of indoleamine 2,3-dioxygenase (IDO), and their structure-activity relationship was explored. Coupling reactions between various benzenesulfonyl chlorides and phenylhydrazides were utilized to synthesize the sulfonylhydrazides bearing various substituents. Compound 3i exhibited 61 nM of IC50 in enzymatic assay and 172 nM of EC50 in the HeLa cell. The computational study of 3i suggested that the major interactions between 3i and IDO protein are the coordination of sulfone and heme iron, the hydrogen bonding and hydrophobic interactions between 3i and IDO. This novel class of IDO inhibitor provides a new direction to discover effective anti-cancer agents.

SIMPLE PREPARATION OF N-ALKYL-N-ARYLHYDRAZINES FROM DIAZOTABLE N-ARYLAMINES

Phase-Transfer-catalyzed N-alkylation of arylhydrazones 2, followed by hydrazinolysis with hydrazine hydrate in the presence of concentrated hydrochloric acid, provides a new access to N-alkyl-N-arylhydrazines 3.

The Crystal Structures of (Z)-Dimethyl 3-Methoxycarbonylmethyl-11-methyl-2-oxo-1,4,5,6,6a,11-hexahydrofurocyclohexaindol-6a-ylfumarate, (E)-Dimethyl-3-methoxycarbonylmethyl-12-methyl-2-oxo-4,5,6,7,7a,12-hexahydro-1H-furocycloh

The structures of two (1 IND + 2 DMAD -CH2) adducts, and a (1 IND + 2 DMAD - CH4O) adduct, obtained from the addition of dimethyl acetylenedicarboxylate (DMAD) to N-methylindoles (IND) having a polymethylene chain linking positions 2 and 3, have been dete