A novel approach to 5H-pyrazino[2,3-b]indoles via annulation of 3-diazoindolin-2-imines with 2H-azirines or 5-alkoxyisoxazoles under Rh(ii) catalysis

Literature Information

Publication Date 2017-11-30
DOI 10.1039/C7OB02637D
Impact Factor 3.876
Authors

Julia O. Ruvinskaya, Nikolai V. Rostovskii, Ilya P. Filippov, Alexander F. Khlebnikov, Mikhail S. Novikov


View Original

Abstract

A novel one-step method for the preparation of 5H-pyrazino[2,3-b]indoles with different substitution patterns in all rings of the tricyclic system via the Rh2(OAc)4-catalyzed reaction of 2H-azirines with 3-diazoindolin-2-imines is reported. Alkyl 5H-pyrazino[2,3-b]indole-3-carboxylates were also prepared by a one-pot procedure from synthetic equivalents of alkyl 2H-azirine-2-carboxylates, 5-alkoxyisoxazoles. The reactions provide the first examples of the use of Rh(II) catalysis for intermolecular annulations with 2H-azirines and isoxazoles.

Related Literature

Back cover

Front/Back Matter

DOI: 10.1039/C2CP90039D

Front cover

Cover

DOI: 10.1039/C2CP90002E

The interaction of His337 with the Mn4Ca cluster of photosystem II

Simon Petrie, Phillip Gatt, Robert Stranger, Ron J. Pace

2012-02-13 Paper

DOI: 10.1039/C2CP23935C

The electric field as a novel switch for uptake/release of hydrogen for storage in nitrogen doped graphene

Z. M. Ao, F. M. Peeters, S. Li

2011-11-21 Paper

DOI: 10.1039/C1CP23153G

Back matter

Front/Back Matter

DOI: 10.1039/C2CP90040H

Polymer dynamics in responsive microgels: influence of cononsolvency and microgel architecture

C. Scherzinger, O. Holderer, D. Richter, W. Richtering

2012-01-17 Paper

DOI: 10.1039/C2CP23328B

The nature of cationic adsorption sites in alkaline zeolites—single, dual and multiple cation sites

P. Nachtigall, M. R. Delgado, D. Nachtigallova, C. O. Arean

2011-11-28 Perspective

DOI: 10.1039/C2CP23237E

Photo-controlled metal-ion (Zn2+ and Cd2+) release in aqueous Tween-20 micelle solution

Xu Zhang, Yi Chen

2012-01-11 Paper

DOI: 10.1039/C2CP23265K

A method for finding the ridge between saddle points applied to rare event rate estimates

Jón Bergmann Maronsson, Hannes Jónsson, Tejs Vegge

2011-12-22 Paper

DOI: 10.1039/C2CP23421A

An operando DRIFTS investigation into the resistance against CO2 poisoning of a Rh/alumina catalyst during toluenehydrogenation

Julien Scalbert, Frederic C. Meunier, Cecile Daniel, Yves Schuurman

2011-10-11 Paper

DOI: 10.1039/C1CP22620G

You might also like

Compound Q&A

What are the main uses of (3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8)?

(3.beta.)-3-Hydroxy-N,N-dimethyl-chol-5-en-24-amide (CAS: 79066-03-8) is primari...

79066-03-8(3.beta.)-3-Hydroxy-...
Compound Q&A

What regulatory guidelines apply to 5-(aminomethyl)-2-methoxyphenol (CAS: 89702-89-6)?

5-(Aminomethyl)-2-methoxyphenol (CAS: 89702-89-6) is classified under GHS as a s...

89702-89-65-(aminomethyl)-2-me...
Compound Q&A

What is Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7)?

Thieno[2,3-c]pyridin-7(6H)-one (CAS: 28981-13-7) is a heterocyclic organic compo...

28981-13-7Thieno[2,3-c]pyridin...
Compound Q&A

Is 1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride (CAS: 1185311-28-7) safe?

1-[(6-Methoxy-3-pyridinyl)methyl]-4-piperidinamine dihydrochloride is generally ...

1185311-28-71-[(6-Methoxy-3-pyri...
Compound Q&A

What regulatory guidelines apply to [(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2)?

[(2E)-3-Phenyl-2-propen-1-yl]phosphonic acid (CAS: 146404-58-2) is regulated und...

146404-58-2[(2E)-3-Phenyl-2-pro...
Compound Q&A

What regulatory guidelines apply to 6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7)?

6-Bromo-7-methoxyquinoline (CAS: 1620515-86-7) falls under the scope of the Glob...

1620515-86-76-Bromo-7-methoxyqui...
Compound Q&A

What industries use (2R)-1-(1-Benzofuran-2-yl)-N-propyl-2-pentanamine (CAS: 260550-89-8)?

This compound is primarily used in the pharmaceutical industry for the developme...

260550-89-8(2R)-1-(1-Benzofuran...
1228013-15-71-Ethyl-7-[2-methyl-...
Compound Q&A

Are there alternatives to {5-(Acryloylamino)-2-[(dimethylamino)methyl]phenyl}boronic acid (CAS: 1217500-78-1) in synthesis?

Alternative reagents such as 2-[(dimethylamino)methyl]phenylboronic acid or rela...

1217500-78-1{5-(Acryloylamino)-2...
Compound Q&A

What is 3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2)?

3-(Piperidin-4-yloxy)pyridine (CAS: 310881-48-2) is an organic compound with the...

310881-48-23-(Piperidin-4-yloxy...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.