Synthesis of functionalized 2,5-dihydropyrrole derivatives via a convenient [3 + 2] annulation of azomethine ylides with allenoates

Literature Information

Publication Date 2018-08-28
DOI 10.1039/C8OB01946K
Impact Factor 3.876
Authors

Zhusheng Huang, Zonghao Dai, Jin Zhu, Fulai Yang, Qingfa Zhou


View Original

Abstract

A convenient [3 + 2] annulation of azomethine ylides with allenoates promoted by triethylamine produced highly functionalized 2,5-dihydropyrrole derivatives in moderate to excellent yields under mild conditions. The potential utility of this reaction indicates that this reaction could be performed on the gram scale and the synthesized functionalized 2,5-dihydropyrrole derivatives could be further transformed into other interesting heterocycles. The mechanism for the transformation is a tandem β-addition/Mannich cyclization process.

Related Literature

High-level QM/MM modelling predicts an arginine as the acid in the condensation reaction catalysed by citrate synthase

Marc W. van der Kamp, Adrian J. Mulholland

2008-03-11 Communication

DOI: 10.1039/B800496J

Construction of aryl-substituted triquinanes through the interrupted Nazarov reaction

Curtis J. Rieder, Ryan J. Fradette, F. G. West

2008-02-25 Communication

DOI: 10.1039/B800800K

A DNAzyme cascade for the amplified detection of Pb2+ ions or l-histidine

Johann Elbaz, Bella Shlyahovsky, Itamar Willner

2008-01-31 Communication

DOI: 10.1039/B716774A

Isolation and X-ray structural characterization of tetraisopropylpyrene cation radical

Moloy Banerjee, Vijay S. Vyas, Sergey V. Lindeman, Rajendra Rathore

2008-02-28 Communication

DOI: 10.1039/B800168E

Photoinduced CO release, cellular uptake and cytotoxicity of a tris(pyrazolyl)methane (tpm) manganese tricarbonyl complex

Johanna Niesel, Antonio Pinto, Harmel W. Peindy N'Dongo, Klaus Merz, Ingo Ott, Ronald Gust, Ulrich Schatzschneider

2008-02-08 Communication

DOI: 10.1039/B719075A

Synthesis and properties of trifluoroethoxy-coated binuclear phthalocyanine

Hideyuki Yoshiyama, Norio Shibata, Takefumi Sato, Shuichi Nakamura, Takeshi Toru

2008-03-28 Communication

DOI: 10.1039/B800918J

Exploring the relationship between cocrystal stability and symmetry: is Wallach's rule applicable to multi-component solids?

Tomislav Friščić, László Fábián, Jonathan C. Burley, David G. Reid, Melinda J. Duer, William Jones

2008-01-30 Communication

DOI: 10.1039/B717532A

Self-assembly of a peptide rod–coil: a polyproline rod and a cell-penetrating peptide Tat coil

You-Rim Yoon, Yong-beom Lim, Eunji Lee, Myongsoo Lee

2008-03-11 Communication

DOI: 10.1039/B719868J

Rational design of supramolecular chirality in porphyrin assemblies: the halogen bond case‡

Sankar Muniappan, Sophia Lipstman, Israel Goldberg

2008-02-14 Communication

DOI: 10.1039/B719625C

Highly luminescent mono- and multilayers of immobilized CdTe nanocrystals: controlling optical properties through post chemical surface modification

Takaaki Tsuruoka, Rena Takahashi, Toshihiro Nakamura, Minoru Fujii, Kensuke Akamatsu, Hidemi Nawafune

2008-01-29 Communication

DOI: 10.1039/B717732A

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

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.