101471-08-3

Upstream product

• 40940-64-5 (±)-6-bromo-1-phenylcyclohex-1-ene 
• 771-98-2 1-Phenylcyclohexene 
• 116316-18-8 Phenylselenenyl azide 
• 507237-57-2 6-bromo-2,3,4,5-tetrahydro-1,1'-biphenyl 
• 100-58-3 phenylmagnesium bromide 
• 32363-86-3 2-phenylcyclohex-2-enol 
• 40940-63-4 1-phenyl-2-bromo-1-hydroxycyclohexane 
• 563-63-3 silver(I) acetate 

Relevant academic research and scientific papers

Copper-catalyzed cascade click/nucleophilic substitution reaction to access fully substituted triazolyl-organosulfurs

A novel cascade click/nucleophilic substitution reaction is developed to access 4-heterofunctionalized fully substituted triazolyl-organosulfurs using thiocyanates as both leaving groups and organosulfur precursors. This method features high regioselectivities and board substrate scope. 33 examples are shown to demonstrate the structural diversity through the synthesis of fully substituted triazolyl-organosulfurs including triazolyl-thiocyanates, triazolyl-sulfinylcyanides, triazolyl-thioethers, triazolyl-thiols and triazolyl-disulfides from internal thiocyanatoalkynes.

Nucleophilic Attack on Iodonium Ion Intermediate. "Real" Regiochemistry of the Iodo Azide Adduct of 1-Phenylcyclohexene and of Its Dehydrohalogenation Product

The regiochemistry of the anti iodo azide adduct (IAA) of 1-phenylcyclohexene (1), originally reported as 3, was reexamined and proposed to be the reversed one 4 on the basis of its dehydrohalogenation to an unsaturated compound, which was supposed to be the azido olefin 8.Structural data on the anti iodo isocyanate adduct of 1 (5) prompted us to further verify the regiochemistry of the IAA.Comparison of NMR data (1H and 13C) of the IAA with corresponding ones of analogous compounds of proved structures and the absence of any coupling in the 15N NMR of the IAA led us to reverse further the regiochemistry of the IAA to the original one 3.The dehydrohalogenation product of the IAA was proven to be different from 8 and was unequivocally shown to be the isomeric azido olefin 14.The formation of 14 from 3 (IAA) was rationalized through the initial formation of the azido olefin 16, followed by a sigmatropic rearrangement to the more stable isomeric 14.

Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.

Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would

Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation

The catalytic enantioselective preparation of densely functionalized amines is a fundamental synthetic challenge. To address this challenge, we report for the first time that the Winstein rearrangement can be enlisted as the racemization pathway in a dynamic kinetic resolution of allylic azides. Alkene functionalization by Sharpless dihydroxylation affords tertiary azides in excellent enantioselectivity (up to 99:1 er). This approach establishes the chirality of the tertiary azide, obviates the need to directly forge either a congested C-N or C-C bond at the new nitrogenous stereocenter, and establishes additional functionality. Several examples demonstrate further elaboration of this functionality.

Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis

Efficient and rapid synthesis of 1,2,3-triazole derivatives has been achieved via Huisgen's 1,3-dipolar cycloaddition between alkyl/arylazides and diethyl/dimethyl acetylenedicarboxylate in excellent yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the prevailing time-consuming solution phase protocols and affords the triazoles just in 1-3 min. In vitro antitubercular activity of these triazoles was screened against Mycobacterium tuberculosis H37Rv strain. Four of the compounds showed MIC in the range of 1.56-3.13 μg/mL proving their potential activity.

Regiochemistry of Additions of Iodine Azide to 1-Arylcyclohexanes

The addition products of iodine azide to several 1-arylcyclohexanes have been shown to be 2-azido-1-iodo-1-arylcyclohexanes and not 1-azido-2-iodo-1-arylcyclohexanes as reported by Hassner et al.