An Efficient Synthesis of <i>N</i>-Arylputrescines and Cadaverines

Link, Natalia P.; Díaz, Jimena Estela; Orelli, Liliana R.

doi:10.1055/s-0028-1087817

Cited by 4 publications

(3 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The ω - arylaminonitrile precursors were obtained by reaction of the corresponding ω-halonitrile and arylamines, as previously reported by our group [44]. …”

Section: Resultsmentioning

confidence: 99%

Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes

Díaz¹,

Mollo²,

Orelli³

2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe first general procedure for the synthesis of 5 to 7-membered 1-aryl-2-iminoazacycloalkanes is presented, by microwave-assisted ring closure of ω-arylaminonitriles promoted by polyphosphoric acid (PPA) esters. 1-Aryl-2-iminopyrrolidines were easily prepared from the acyclic precursors employing a chloroformic solution of ethyl polyphosphate (PPE). The use of trimethylsilyl polyphosphate (PPSE) in solvent-free conditions allowed for the synthesis of 1-aryl-2-iminopiperidines and hitherto unreported 1-aryl-2-iminoazepanes. The cyclization reaction involves good to high yields and short reaction times, and represents a novel application of PPA esters in heterocyclic synthesis.

show abstract

“…The ω - arylaminonitrile precursors were obtained by reaction of the corresponding ω-halonitrile and arylamines, as previously reported by our group [44]. …”

Section: Resultsmentioning

confidence: 99%

Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes

Díaz¹,

Mollo²,

Orelli³

2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…In tetrahydrofuran (THF), acetonitrile, and dimethoxyethane, very low conversion to the desired product was observed. In previous work, we demonstrated that potassium and sodium iodides significantly improve the yields of nucleophilic substitutions, [24] probably because of in situ generation of a more reactive iodoalkyl compound. To test this hypothesis, we next explored potassium and sodium iodides as catalysts.…”

Section: Synthesis Of Phosphonoacetamidesmentioning

confidence: 93%

Microwave-Enhanced Synthesis of Phosphonoacetamides

Gruber

Mollo

Zani

et al. 2011

Synthetic Communications

View full text Add to dashboard Cite

An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono)acetamides 1, by reaction of chloro-and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.

show abstract

“…Compounds ( 1 , 5 , 7 , 9 , 10 – 12 , 14 – 15 , 27 , 29 , 33 , 34 , 36 , 37 ), 3 18 , 31 ( 19 , 21 ), 32 22 , 33 ( 23 , 31 , 32 ) 34 were described in the literature.…”

Section: Methodsmentioning

confidence: 99%

Conformational and Stereodynamic Behavior of Five- to Seven-Membered 1-Aryl-2-iminoazacycloalkanes

et al. 2019

View full text Add to dashboard Cite

The stereodynamic behavior of 1-arylpyrrolidin-2-imines, having a C aryl –N stereogenic axis, has been studied by means of dynamic nuclear magnetic resonance and density functional theory calculations, evaluating the steric effect of ortho -aryl substituents. The rotational barrier due to E / Z isomerism about the −C=N–H bond was also determined. The dynamic stereochemistry of homologous six- and seven-membered iminoazacycloalkane rings and their oxo-analogues was also comparatively investigated, evidencing a ring size effect. It was found that the seven-membered heterocycle shows additional dynamic features because of ring inversion.

show abstract

An Efficient Synthesis of N-Arylputrescines and Cadaverines

Cited by 4 publications

References 5 publications

Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes

Microwave-assisted cyclizations promoted by polyphosphoric acid esters: a general method for 1-aryl-2-iminoazacycloalkanes

Microwave-Enhanced Synthesis of Phosphonoacetamides

Conformational and Stereodynamic Behavior of Five- to Seven-Membered 1-Aryl-2-iminoazacycloalkanes

Contact Info

Product

Resources

About