Metal-free construction of dihydropyrazino[2,3-<i>b</i>]indoles from 2-aminoacetophenones, isocyanates and 1,2-diamines

Fang, Jingxi; Fang, Jiayao; Rao, Yingbo; Qiu, Huanyi; Pan, Zhentao; Ma, Yongmin

doi:10.1039/d3ob01967e

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01967e

|View full text |Cite

Metal-free construction of dihydropyrazino[2,3-b]indoles from 2-aminoacetophenones, isocyanates and 1,2-diamines

Jingxi Fang,

Jiayao Fang,

Yingbo Rao

et al.

Abstract: A novel metal-free and mild strategy for the construction of dihydropyrazino[2,3-b]indoles in 2-MeTHF as a green solvent at room temperature is described.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article5

Relationship

Self Cite2

Independent3

Authors

Journals

Cited by 6 publications

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using N,N‐Dimethylethanolamine as a Single/Triple Carbon Synthon

Zhang,

Chen,

Chen

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

An efficient and regioselective cyclization for construction of pyrazolo[3,4‐b]pyridines and methylene‐bridged bis(pyrazolo[1,5‐a]pyrimidines) has been established. It involves a [3+2+1] annulation of 3(5)‐aminopyrazole and N,N‐dimethylethanolamine (DMEA) with 1,2‐insertion of aryl methyl ketones or 2,1‐insertion of aryl alkynes. DMEA is oxidized through C(sp3)‐H activation to provide a single or triple carbon source.

show abstract

Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using N,N‐Dimethylethanolamine as a Single/Triple Carbon Synthon

Zhang,

Chen,

Chen

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

Direct ortho‐Selective Amination of Naphthols with Nitroarenes through Transfer‐Hydrogenation

Ma,

Zhang,

Xia

et al. 2024

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

Hydrogen atom transfer from commonly used solvents to nitroarenes occurred. Such solvents required C(sp3)H‐C(sp3)H bond adjacent to oxygen atoms, such as 1,4‐dioxane, tetrahydrofuran, alkanol, ethylene glycol, glycerol and bis(2‐methoxyethyl) ether. The transformation was transition‐metal free and the reduced nitroarenes were trapped by naphthols and their analogues at ortho‐position. The protocol provided a favourable and efficient route to access ortho‐arylaminonaphthols and a possible mechanism is depicted.

show abstract

Efficient access to spiro[quinazoline-thiophen](thi)ones via acetic acid mediated [3 + 2] annulation of quinazolin(thi)one enamines with dithianediol

Fang,

Pan,

Rao

et al. 2024

Tetrahedron Letters

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Metal-free construction of dihydropyrazino[2,3-b]indoles from 2-aminoacetophenones, isocyanates and 1,2-diamines

Abstract: A novel metal-free and mild strategy for the construction of dihydropyrazino[2,3-b]indoles in 2-MeTHF as a green solvent at room temperature is described.

Cited by 6 publications

References 45 publications

Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using N,N‐Dimethylethanolamine as a Single/Triple Carbon Synthon

Regioselective Annulation of 3(5)‐Aminopyrazole with Aryl Ketones or Aryl Alkynes Using N,N‐Dimethylethanolamine as a Single/Triple Carbon Synthon

Direct ortho‐Selective Amination of Naphthols with Nitroarenes through Transfer‐Hydrogenation

Efficient access to spiro[quinazoline-thiophen](thi)ones via acetic acid mediated [3 + 2] annulation of quinazolin(thi)one enamines with dithianediol

Contact Info

Product

Resources

About