74965-38-1

Usage

Uses

Used in Pharmaceutical Industry:
2-BOC-AMINO-BENZALDEHYDE is used as a key intermediate for the synthesis of various pharmaceuticals. Its presence in the molecular structure allows for the creation of complex organic compounds that can be tailored for specific therapeutic applications, such as the development of new drugs with unique mechanisms of action.
Used in Agrochemical Industry:
In the agrochemical sector, 2-BOC-AMINO-BENZALDEHYDE is employed as a building block for the preparation of agrochemicals. Its versatility in chemical reactions facilitates the design and synthesis of novel compounds with potential applications in crop protection, pest control, and other agricultural areas.
Used in Organic Synthesis:
2-BOC-AMINO-BENZALDEHYDE is used as a versatile building block in organic synthesis. Its ability to undergo various chemical reactions makes it an indispensable tool for the creation of complex organic compounds, which can be further utilized in the development of new materials, catalysts, and other specialty chemicals.

InChI:InChI=1/C12H15NO3/c1-12(2,3)16-11(15)13-10-7-5-4-6-9(10)8-14/h4-8H,1-3H3,(H,13,15)

Upstream product

• 3422-01-3 tert-butyl phenylcarbamate 
• 68-12-2 N,N-dimethyl-formamide 
• 164226-32-8 2-(tert-butyloxycarbonyl)aminobenzyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 552-89-6 2-nitro-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 62-53-3 aniline 
• 34619-03-9 tert-butyldicarbonate 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 24608-52-4 tert-butyl chloroformate 
• 118-92-3 anthranilic acid 
• 612-25-9 2-Nitrobenzyl alcohol 

Downstream Products

• 217300-86-2 N-<(2'-nitrostilben-2-yl)phenyl>-tert-butylcarbamate 
• 1312706-36-7 C₁₂H₁₆N₂O₃ 
• 1394031-49-2 tert-butyl 2-benzoylindoline-1-carboxylate 
• 1435944-09-4 tert-butyl 2-(3-(4-methoxyphenyl)-3-oxopropyl)phenylcarbamate 
• 1435944-10-7 tert-butyl 2-(3-oxo-3-p-tolylpropyl)phenylcarbamate 
• 1435944-11-8 tert-butyl (2-(3-(4-fluorophenyl)-3-oxopropyl)phenyl)carbamate 
• 1435944-12-9 tert-butyl 2-(3-(4-chlorophenyl)-3-oxopropyl)phenylcarbamate 
• 1435944-13-0 tert-butyl 2-(3-(furan-2-yl)-3-oxopropyl)phenylcarbamate 
• 1435944-14-1 tert-butyl 2-(3-oxo-3-(thiophen-2-yl)propyl)phenylcarbamate 
• 1435944-15-2 tert-butyl 2-(3-(naphthalen-2-yl)-3-oxopropyl)phenylcarbamate 
• 1435944-16-3 tert-butyl 2-(4-methyl-3-oxopentyl)phenylcarbamate 
• 1435944-17-4 tert-butyl 2-(4,4-dimethyl-3-oxopentyl)phenylcarbamate 
• 1435944-20-9 tert-butyl 2-(4-methoxybenzoyl)indoline-1-carboxylate 
• 1435944-21-0 tert-butyl 2-(4-methylbenzoyl)indoline-1-carboxylate 

Relevant academic research and scientific papers

Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines

A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.

A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines

We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.

4CzIPN catalyzed photochemical oxidation of benzylic alcohols

A green photoredox oxidation of benzylic primary and secondary alcohols to aldehydes and ketones with air as an oxidant was reported. The oxidation shows broad substrate scope and excellent selectivity over benzylic alcohols to the aliphatic alcohols. Further mechanistic studies revealed a quinuclidine mediated HAT process, and blue LEDs promoted 4CzlPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) photoredox cycle were involved in our oxidation.

Designing and Accurately Developing a [6 + 2] Dipolar Cycloaddition for the Synthesis of Benzodiazocines

1,6-Dipolar cycloadditions represent a valuable strategy for the rapid construction of medium-sized rings. Herein, we describe the concept for the design of 1,6-dipoles that bypasses the regioselectivity. Through the introduction of an amino group into Morita-Baylis-Hillman (MBH) carbonates, unprecedented [6 + 2] dipolar cycloadditions were accurately developed with Cs2CO3, efficiently delivering a series of benzodiazocines in mild conditions. Computational studies bring a deeper understanding of this reaction.

DABCO catalyzed [4+2] annulations of Morita-Baylis-Hillman carbonates with isocyanates

A highly concise method for 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed [4+2] annulations ofo-amino-acylation of aryl MBH carbonates with isocyanates has been developed. For the first time, MBH carbonates served as 1,4-dipoles, providing functionalized 3,4-dihydroquinazolinones in mild conditions with good to excellent yields. The density functional theory calculations of the mechanism supports our hypothesis.

Iron-Catalyzed Reductive Cyclization by Hydromagnesiation: A Modular Strategy Towards N-Heterocycles

A reductive cyclization to prepare a variety of N-heterocycles, through the use of ortho-vinylanilides, is reported. The reaction is catalyzed by an inexpensive and bench-stable iron complex and generally occurs at ambient temperature. The transformation likely proceeds through hydromagnesiation of the vinyl group, and trapping of the in situ generated benzylic anion by an intramolecular electrophile to form the heterocycle. This iron-catalyzed strategy was shown to be broadly applicable and was utilized in the synthesis of substituted indoles, oxindoles and tetrahydrobenzoazepinoindolone derivatives. Mechanistic studies indicated that the reversibility of the hydride transfer step depends on the reactivity of the tethered electrophile. The synthetic utility of our approach was further demonstrated by the formal synthesis of a reported bioactive compound and a family of natural products.

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade

An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.

Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction

A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.

Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives

A Pd-catalyzed, highly regioselective and stereoselective three-component domino allylic substitution/N-H carbene insertion reaction under mild conditions is described. This reaction demonstrates a wide substrate scope and satisfactory functional group tolerance, providing a broad range of allylic sulfone-containing amino acid derivatives. Moreover, DBU mediates highly diastereoselective cross-dehydrogenative coupling annulation of allylic sulfones without using peroxides or any metal oxidants. This developed protocol affords 7-membered ring heterocyclic compounds incorporating both sulfone-containing amino acid esters and one quaternary carbon center. Mechanistic studies indicate that an unusual umpolung of glycine occurred in this annulation.