Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE)

2018 ◽  
Vol 83 (17) ◽  
pp. 9707-9717 ◽  
Author(s):  
Angelina Osipyan ◽  
Alexander Sapegin ◽  
Alexander S. Novikov ◽  
Mikhail Krasavin
Synthesis ◽  
2021 ◽  
Author(s):  
Sergey Grintsevich ◽  
Alexander V. Sapegin ◽  
Andrzej Bojarski ◽  
Beata Duszyńska ◽  
Mikhail Krasavin

Attempts to extend the hydrated imidazoline ring expansion (HIRE) strategy to a series of diarene-fused [1,4]diazepinones (earlier applied successfully to bis-pyrido substrate nevirapine) resulted in no ring expansion but rather 2-aminoethyl side chain expulsion. This seeming setback (setting the limitations to the HIRE methodology substrate scope) led to the discovery of selective dopamine D2 ligands with elements of structure-activity relationships.


2020 ◽  
Vol 61 (42) ◽  
pp. 152423
Author(s):  
Kseniya Lavit ◽  
Elena Reutskaya ◽  
Sergey Grintsevich ◽  
Alexander Sapegin ◽  
Mikhail Krasavin

2017 ◽  
Vol 15 (14) ◽  
pp. 2906-2909 ◽  
Author(s):  
Alexander Sapegin ◽  
Angelina Osipyan ◽  
Mikhail Krasavin

A facile approach to hitherto unknown ten-membered ring systems via a hydrolytic imidazoline ring expansion (HIRE) is described. Medium-sized rings are scarce in the contemporary medicinal chemistry toolbox. The new HIRE strategy broadens the arsenal of synthetic methods to obtain such scaffolds.


Author(s):  
Sergey Grintsevich ◽  
Alexander Sapegin ◽  
Elena Reutskaya ◽  
Stefan Peintner ◽  
Máté Erdélyi ◽  
...  

2018 ◽  
Vol 84 (4) ◽  
pp. 1693-1705 ◽  
Author(s):  
Elena Reutskaya ◽  
Angelina Osipyan ◽  
Alexander Sapegin ◽  
Alexander S. Novikov ◽  
Mikhail Krasavin

2020 ◽  
Vol 2020 (35) ◽  
pp. 5635-5635
Author(s):  
Sergey Grintsevich ◽  
Alexander Sapegin ◽  
Elena Reutskaya ◽  
Stefan Peintner ◽  
Máté Erdélyi ◽  
...  

2020 ◽  
Author(s):  
Nathan O'Brien ◽  
Naokazu Kano ◽  
Nizam Havare ◽  
Ryohei Uematsu ◽  
Romain Ramozzi ◽  
...  

<div>The isolation and reactivities of two pentacoordinated phosphorus–tetracoordinated boron bonded compounds were</div><div>explored. A strong Lewis acidic boron reagent and electron-withdrawing ligand system were required to form the</div><div>pentacoordinated phosphorus state of the P–B bond. The first compound, a phosphoranyl-trihydroborate, gave a THF</div><div>stabilised phosphoranyl-borane intermediate upon a single hydride abstraction in THF. This compound could undergo a</div><div>unique rearrangement reaction, that involved a two-fold ring expansion, to give an unusual fused bicyclic compound or it</div><div>could act as a mono-hydroboration reagent. The hydroboration reactivity of the intermediate was found to be more reactive</div><div>towards alkynes over alkenes with good to moderate regioselectivity towards the terminal carbon. The second compound,</div><div>a phosphoranyl-triarylborate, was found to have a vastly different reactivity to the trihydroborate as it was highly stable</div><div>towards acids and bases. This is thought to be due to the large bulk around the P–B bond as shown in the crystal structure</div>


Author(s):  
Hannah E. Burdge ◽  
Takuya Oguma ◽  
Takahiro Kawajiri ◽  
Ryan Shenvi

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>


2019 ◽  
Author(s):  
Hannah E. Burdge ◽  
Takuya Oguma ◽  
Takahiro Kawajiri ◽  
Ryan Shenvi

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>


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