58028-75-4

Upstream product

• 111-49-9 hexamethylene imine 
• 446-52-6 2-Fluorobenzaldehyde 

Downstream Products

• 58028-83-4 4-(2-azepan-1-yl-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 130084-33-2 (E)-2-(Perhydroazepin-1-yl)benzaldoxim 
• 1092982-50-7 6-benzyl-5,6,6a,7,8,9,10,11-octahydroazepino[1,2-a]quinazoline 
• 1092982-51-8 6-(4-bromophenyl)-5,6,6a,7,8,9,10,11-octahydroazepino[1,2-a]quinazoline 
• 1097259-57-8 dimethyl 2-(2-(azepan-1-yl)benzylidene)malonate 
• 1187891-56-0 (E)-3-(3-(2-(azepan-1-yl)phenyl)acryloyl)oxazolidin-2-one 
• 1285444-63-4 C₂₀H₂₅N₃O₂S 
• 1361537-95-2 N-(2-(azepan-1-yl)benzylidene)-2-phenylaziridin-1-amine 
• 40832-99-3 N-phenylazepane 

Relevant academic research and scientific papers

Catalyst-free photodecarbonylation ofortho-amino benzaldehyde

It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.

Hexafluoroisopropanol-Mediated Redox-Neutral α-C(sp3)-H Functionalization of Cyclic Amines via Hydride Transfer

Hexafluoroisopropanol has been demonstrated as the versatile promoter for redox-neutral α-C(sp3)-H functionalization of cyclic amines via the cascade [1,5]-hydride transfer/cyclization strategy. A wide range of cyclic amines are functionalized

N-Alkylation-Initiated Redox-Neutral [5 + 2] Annulation of 3-Alkylindoles with o-Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines

Described herein is an unprecedented N-Alkylation-initiated redox-neutral [5 + 2] annulation of 3-Alkylindoles with o-Aminobenzaldehydes via a cascade N-Alkylation/dehydration/[1,5]-hydride transfer/Friedel-Crafts alkylation sequence. A series of indole-1,2-fused 1,4-benzodiazepines are facilely constructed in moderate to good yields in one step. This protocol features excellent regioselectivity, metal-free conditions, high step economy, and wide substrate scope.

Investigation of the [1,5]-hydride shift as a route to nitro-Mannich cyclisations

Conditions were found for the [1,5]-hydride shift nitro-Mannich reaction that led to the synthesis of 2,3-disubstituted tetrahydroquinolines. Two simple cyclic amine substrates gave diastereomerically pure rearranged products in 65 and 90% yields by refluxing in HFIP. A more general procedure used Gd(OTf)3 as a catalyst and successfully rearranged other cyclic and acyclic amines in 42–84% yield with diastereomeric ratios of 75:25 to >95:5 in favour of the anti-diastereoisomer (9 examples). Two examples of sulphur containing heterocycles gave lower yields of 9 and 25%. Electron withdrawing substituents were shown to have a deleterious effect on the success of the reaction. The results indicated the limitation of the [1,5]-hydride shift nitro-Mannich reaction with respect to the stability of the intermediate iminium ion.

Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines

The redox-neutral cascade dearomatization of indoles with o-aminobenzaldehydes has been realized via the hydride transfer strategy, achieving the condition- A nd substrate-controlled divergent synthesis of tetrahydroquinoline-fused spiroindolenines. The integration of hydride transfer-involved C(sp3)-H functionalization with dearomatization provides a promising platform for the construction of structurally diverse molecules.

Expedient synthesis of tetrahydroquinoline-3-spirohydantoin derivatives: Via the Lewis acid-catalyzed tert -amino effect reaction

Magnesium triflate was found to effectively catalyze the tert-amino effect reaction (T-reaction) involving ethyl 3-(2-(dialkylamino)-phenyl)-2-nitroacrylates leading to tetrahydroquinoline nitroester derivatives. These compounds can be readily transformed

Novel, versatile three-step synthesis of 1,2,3,4,10,10a-hexahydro- pyrazino[1,2- a ]indoles by intramolecular carbene-mediated C-H insertion

A new convenient three-step synthesis of the privileged CNS scaffold 1,2,3,4,10,10a-hexahydropyrazino[1,2-a]indoles has been developed. The method makes use of an intramolecular carbene-mediated C-H insertion in phenylpiperazine-derived tosyl-hydrazones m

tert-Amino effect in heterocyclic chemistry. Synthesis of hydrogenated spiro derivatives of quinolines

A new method was developed for the one-step synthesis of spiro derivatives of fused quinolines by the reactions of ortho-amino derivatives of benzaldehyde with Meldrum's acid, cyclohexane-1,3-dione, or N,N′-disubstituted barbituric acids.