Rethinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side-Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffolds

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

An attempt at the hydrated imidazoline ring expansion (HIRE) of diarene-fused [1,4]diazepinones delivers selective dopamine D2 receptor ligands

Synthesis ◽  
2021 ◽  
Author(s):  
Sergey Grintsevich ◽  
Alexander V. Sapegin ◽  
Andrzej Bojarski ◽  
Beata Duszyńska ◽  
Mikhail Krasavin
Keyword(s):  
Dopamine D2 Receptor ◽  
D2 Receptor ◽  
Ring Expansion ◽  
Side Chain ◽  
Receptor Ligands ◽  
Structure Activity Relationships ◽  
Dopamine D2 ◽  
Structure Activity ◽  
Imidazoline Ring ◽  
Selective Dopamine

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.

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
Keyword(s):  
Ring Expansion ◽  
Imidazoline Ring

Free-Radical Polymerization and Ring-Expansion of a Cubane Acrylate: a Unique Low-Shrink Polymer

2009 ◽  
Vol 62 (2) ◽  
pp. 145 ◽  
Author(s):  
Alison E. McGonagle ◽  
G. Paul Savage
Keyword(s):  
Free Radical ◽  
Radical Polymerization ◽  
Ring Opening ◽  
Free Radical Polymerization ◽  
Ring Expansion ◽  
Side Chain ◽  
Molecular Volume ◽  
Acrylate Polymer

A pendant cubane substituent has been incorporated into an acrylate polymer side chain to give poly[methyl 4-(acryloyloxymethyl)cubane carboxylate]. Treating this polymer with a rhodium(i) salt triggers a catalytic, ring-opening rearrangement of the cubane substructure to cyclooctatetraene, with a concomitant expansion in molecular volume. This system offers a unique opportunity to reverse the shrinkage associated with polymerization.

scholarly journals Synthesis of a New Type of Trans-Decalin Vitamin D Analogue through a Dyotropic Ring Expansion

2021 ◽  
Vol 2021 ◽  
pp. 1-5
Author(s):  
Hugo Santalla ◽  
Uxía Gómez-Bouzó ◽  
Irene Sánchez-Sanz ◽  
Yagamare Fall
Keyword(s):  
Vitamin D ◽  
Research Group ◽  
Ring Expansion ◽  
Ring System ◽  
Side Chain ◽  
Sulphur Atom ◽  
Mild Conditions ◽  
New Type ◽  
Vitamin D Analogue

A new vitamin D analogue with a trans-fused decalin as the CD-ring system and containing a sulphur atom in the side chain has been synthesized in our research group. The obtention of this analogue is based on a recently discovered transformation of hydrindane cores into decalins through a dyotropic ring expansion in very mild conditions.

Unexpected Ring Expansion of the (3aS,6aR)-γ-Thiolactone Moiety during the Introduction of the (+)-Biotin Side Chain

2009 ◽  
Vol 92 (7) ◽  
pp. 1445-1449 ◽  
Author(s):  
Jian Huang ◽  
Fei Xiong ◽  
Zhong-Hua Wang ◽  
Fen-Er Chen
Keyword(s):  
Ring Expansion ◽  
Side Chain

Zooming in on the hydrated imidazoline ring expansion: Factors influencing the rate of N → N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines

2020 ◽  
Vol 61 (42) ◽  
pp. 152423
Author(s):  
Kseniya Lavit ◽  
Elena Reutskaya ◽  
Sergey Grintsevich ◽  
Alexander Sapegin ◽  
Mikhail Krasavin
Keyword(s):  
Ring Expansion ◽  
Factors Influencing ◽  
Imidazoline Ring

Enzymatic ring expansion of penicillins to cephalosporins: side chain specificity

1987 ◽  
pp. 374 ◽  
Author(s):  
Jack E. Baldwin ◽  
Robert M. Adlington ◽  
Janice B. Coates ◽  
M. James C. Crabbe ◽  
John W. Keeping ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Side Chain

scholarly journals Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

2017 ◽  
Vol 15 (14) ◽  
pp. 2906-2909 ◽  
Author(s):  
Alexander Sapegin ◽  
Angelina Osipyan ◽  
Mikhail Krasavin
Keyword(s):  
Medicinal Chemistry ◽  
Ring Expansion ◽  
Membered Ring ◽  
Synthetic Methods ◽  
Ring Systems ◽  
New Hire ◽  
Imidazoline Ring

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.

ChemInform Abstract: The Enzymatic Ring Expansion of Penicillins to Cephalosporins: Side Chain Specificity.

ChemInform ◽  
1987 ◽  
Vol 18 (45) ◽  
Author(s):  
J. E. BALDWIN ◽  
R. M. ADLINGTON ◽  
M. J. CRABBE ◽  
G. KNIGHT ◽  
T. NOMOTO ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Side Chain
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