Chemistry of 1-aza-1,3-enynes: achievements and key trends of development

Karpov, M. V.; Гарабаджиу, А. В.; Belyaev, A. N.

doi:10.1070/rcr4560

Cited by 2 publications

(2 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1-Aza-1,3-enynes, R 1 -C ≡ C-C(R 2 ) = NR 3 , can be considered as convenient synthons for the directed preparation of polyfunctional compounds, which are of interest to organoelement, pharmaceutical and medical chemistry. [80] To synthesize new polyfunctional and potentially biologically active silatranes bearing the 1-aza-1,3-enyne group we have recently implemented the reaction 3aminopropylsilatrane with propynals of the general formula R-C ≡ C-C(H) = O, where R = Ph, Me 2 C(OH), Me 3 Si, Et 3 Ge. According to data (IR, 1 H, 13 C, 15 N NMR), the obtained compounds 7a-d have a structure shown in Figure 4.…”

Section: New Silatranes and Their Analogsmentioning

confidence: 99%

New atranes and similar ionic complexes. Synthesis, structure, properties

Адамович

2019

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

Section: New Silatranes and Their Analogsmentioning

confidence: 99%

New atranes and similar ionic complexes. Synthesis, structure, properties

Адамович

2019

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Due to their conjugated triple and double bonds, 1-aza-but-1-en-3-ynes 1 form a highly interesting class of compounds with challenging regio- and chemoselectivities in hydroalumination reactions . The polar iminic double bond is expected to induce higher reactivity compared to that of but-1-en-3-ynes like 2 .…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Hydroalumination of 1-Aza-but-1-en-3-ynes (C-Iminoalkynes): Formation of Propargylamines by Imine Reduction and of 5-Aluminazoles and 1-Aza-butadienes by Anti-Michael Attack

et al. 2018

View full text Add to dashboard Cite

Hydroalumination of 1-aza-but-1-en-ynes 1 provides facile access to propargylamines 4 by reduction of the CN bonds or alternatively to 1-aza-buta-1,3-dienes 6 by reduction of the triple bond. The chemoselectivity depends not only on the steric properties of both the hydroalumination agent (di-iso-butylaluminum (DIBAL-H, iBu 2 AlH) versus ditert-butylaluminum hydride (tBu 2 AlH)) and the substrates but also on the reaction temperatures. In several cases, initial aluminum species of 5-aluminazole type 5 could be isolated and characterized by X-ray diffraction, indicating an "anti-Michael" addition of the hydride to the triple bond. Aqueous workup of those species led to 1-azabutadiene derivatives 6. High-level DFT calculations indicate that the observed chemoselectivity is only compatible with a dimeric nature of the hydroaluminating agent. Using such a dimer, the imine reduction corresponds to the kinetically controlled pathway, whereas the triple bond reduction leads to the thermodynamically much more stable 5-aluminazoles, 5.

show abstract

Chemistry of 1-aza-1,3-enynes: achievements and key trends of development

Cited by 2 publications

References 33 publications

New atranes and similar ionic complexes. Synthesis, structure, properties

New atranes and similar ionic complexes. Synthesis, structure, properties

Chemoselective Hydroalumination of 1-Aza-but-1-en-3-ynes (C-Iminoalkynes): Formation of Propargylamines by Imine Reduction and of 5-Aluminazoles and 1-Aza-butadienes by Anti-Michael Attack

Contact Info

Product

Resources

About