Sequential Two‐Fold Claisen Rearrangement, One‐Pot Ring‐Closing Metathesis and Cross‐Metathesis as a Route to Substituted Benzo[b]azepine‐2‐one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

Chattopadhyay, Shital K.; Mandal, Shyamasankar; Banerjee, Joydeep; Maity, Sougata

doi:10.1002/hlca.202000216

Search citation statements

Order By: Relevance

Paper Sections

Select...

-Cyclohexyl-3-((2-methylallyl)oxy)-2-(3-methylbut-2-en-1yl)p...1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2022

2024

Publication Types

Select...

Article3

Book1

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

(1 citation statement)

References 73 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 H NMR (CDCl 3 , 400 MHz):  = 6.33 (d, J = 1.4 Hz, 1 H), 6.31 (d, J = 1.2 Hz, 1 H), 5.25 (tt, J = 7.4 Hz, 1 H), 5. 18…”

Section: -Cyclohexyl-3-((2-methylallyl)oxy)-2-(3-methylbut-2-en-1yl)p...mentioning

confidence: 99%

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Kayser¹,

Nguyen²,

Jordan³

2022

Synthesis

View full text Add to dashboard Cite

An efficient synthesis of 2,5-dihydrobenzoxepine analogues was developed without using protecting groups. Regioselective allylation was optimized through a recent method utilizing magnesium dicarboxylates. Grubbs catalysts were applied to investigate ring-closing metathesis. The scope of the present route was extended to produce four analogues, which provided novel cannabinoid-like 2,5-dihydrobenzoxepines in sufficient quantities to permit in vitro assays on recombinant CB1/CB2 receptors. In vitro assays related to CB1/CB2 receptors did not indicate any activity.

show abstract

“…1 H NMR (CDCl 3 , 400 MHz):  = 6.33 (d, J = 1.4 Hz, 1 H), 6.31 (d, J = 1.2 Hz, 1 H), 5.25 (tt, J = 7.4 Hz, 1 H), 5. 18…”

Section: -Cyclohexyl-3-((2-methylallyl)oxy)-2-(3-methylbut-2-en-1yl)p...mentioning

confidence: 99%

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Kayser¹,

Nguyen²,

Jordan³

2022

Synthesis

View full text Add to dashboard Cite

show abstract

Seven-membered rings

Bissember

Wales

Hawkins

et al. 2023

Progress in Heterocyclic Chemistry

View full text Add to dashboard Cite

Electrochemical Dehydrogenative [3 + 2]/[5 + 2] Annulation of N-Arylacrylamides with γ,σ-Unsaturated Malonates via Direct C(sp³)–H/C(sp²)–H Functionalization

Zhang,

Xu,

Xue

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

Herein, we introduce an electrochemical dehydrogenative [3 + 2]/[5 + 2] annulation of easily available Narylacrylamides with γ,σ-unsaturated malonates through C(sp 3 )−H/C(sp 2 )−H functionalization. The employment of inexpensive ferrocene as the redox catalyst allows access to diverse benzo[b]azepin-2-ones in moderate to excellent yields without stoichiometric oxidants. This protocol features broad substrate scope and excellent selectivity, and mechanistic studies indicated that the reaction proceeded through the oxidation of a C(sp 3 )−H bond to generate an alkyl radical, radical addition across the C�C bond, [3 + 2]/ [5 + 2] annulations, and C(sp 2 )−H functionalization cascades.

show abstract

Sequential Two‐Fold Claisen Rearrangement, One‐Pot Ring‐Closing Metathesis and Cross‐Metathesis as a Route to Substituted Benzo[b]azepine‐2‐one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

Cited by 4 publications

References 73 publications

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Seven-membered rings

Electrochemical Dehydrogenative [3 + 2]/[5 + 2] Annulation of N-Arylacrylamides with γ,σ-Unsaturated Malonates via Direct C(sp³)–H/C(sp²)–H Functionalization

Contact Info

Product

Resources

About

Sequential Two‐Fold Claisen Rearrangement, One‐Pot Ring‐Closing Metathesis and Cross‐Metathesis as a Route to Substituted Benzo[b]azepine‐2‐one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

Cited by 4 publications

References 73 publications

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines

Seven-membered rings

Electrochemical Dehydrogenative [3 + 2]/[5 + 2] Annulation of N-Arylacrylamides with γ,σ-Unsaturated Malonates via Direct C(sp3)–H/C(sp2)–H Functionalization

Contact Info

Product

Resources

About

Electrochemical Dehydrogenative [3 + 2]/[5 + 2] Annulation of N-Arylacrylamides with γ,σ-Unsaturated Malonates via Direct C(sp³)–H/C(sp²)–H Functionalization