345201-68-5

Upstream product

• 612-25-9 2-Nitrobenzyl alcohol 
• 5344-90-1 2-Aminobenzyl alcohol 
• 2937-50-0 Allyl chloroformate 

Downstream Products

• 618113-45-4 (2-chloromethylphenyl)carbamic acid allyl ester 
• 1314234-90-6 prop-2-en-1-yl N-{2-[(3,3-dimethylcycloprop-1-en-1-yl)(hydroxy)methyl]phenyl}-N-(prop-2-en-1-yl)carbamate 
• 1314234-89-3 prop-2-en-1-yl N-(2-formylphenyl)-N-(prop-2-en-1-yl)carbamate 
• 1309934-63-1 prop-2-en-1-yl N-(2-formylphenyl)carbamate 
• 1026796-74-6 {[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-amino}-acetic acid 
• 1026938-60-2 {[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-[2-(2-{(2-tert-butoxycarbonylamino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetylamino)-benzyl]-amino}-acetic acid methyl ester 
• 345201-71-0 {(2-allyloxycarbonylamino-benzyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid methyl ester 
• 345201-72-1 {(2-amino-benzyl)-[(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid methyl ester 
• 345201-70-9 (2-allyloxycarbonylamino-benzylamino)-acetic acid methyl ester 
• 618113-61-4 2-iodomethyl-1-methyl-1,2,3,4-tetrahydroquinoline 
• 618113-50-1 2-bromomethyl-1-methyl-1,2,3,4-tetrahydroquinoline 
• 618113-62-5 2-Iodomethyl-1,2,3,4-tetrahydro-quinoline 

Relevant academic research and scientific papers

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.

A convenient allenoate-based synthesis of 2-quinolin-2-yl malonates and β-ketoesters

N-Protected o-aminobenzaldehydes smoothly react with α,γ-dialkylallenoates under Bronsted basic conditions to yield 2,3-disubstituted quinolines. This three-step reaction cascade of Michael addition, aldol condensation, and 1,3-N → C rearrangement uses the complete protecting group as a building block in a highly efficient C,C-bond formation of a new all-carbon quaternary center. Carbamate protected substrates (N-Boc, N-Cbz, N-Alloc) thus give 2-quinolin-2-yl-malonates, while amide protected substrates (N-Ac, N-Bz) afford 2-quinolin-2-yl-β-ketoesters in high yields.

Oppolzer-type intramolecular Diels-Alder cycloadditions via isomerizations of allenamides

A new approach to Oppolzer's intramolecular Diels-Alder cycloaddition (IMDA) through γ-isomerization of readily available N-tethered allenamides is described. These IMDA reactions are carried out in tandem with the allenamide isomerization or 1,3-H shift,

The aza-xylylene Diels-Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines

The recently discovered intramolecular aza-xylylene Diels-Alder reaction, based on a 1,4-dehydrohalogenation reaction, was extended in terms of substrates and leaving groups allowing the assembly of tetrahydroquinolines in two synthetic steps. Intramolecular cleavage of a thiocarbamate using triphenylphosphine and tetrachloromethane (Appel conditions) to give chloromethyl phenylisocyanate has been presented for the first time. The synthetic feasibility of this process was demonstrated in the first total syntheses of the alkaloids rac-Angustureine and 1-methyl-2-propyltetrahydroquinoline.

Backbone modifications of aromatic peptide nucleic acid (APNA) monomers and their hybridization properties with DNA and RNA

Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-β-alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in triplex formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.