Facile preparation of polycyclic halogen-substituted 1,2,3-triazoles by using intramolecular Huisgen cycloaddition

Literature Information

Publication Date 2023-11-28
DOI 10.1039/D3OB01283B
Impact Factor 3.876
Authors

Kazuki Kobayashi, Nozomi Kasakura, Seiya Kikukawa, Shota Matsumoto, Satoru Karasawa, Takeshi Hata


View Original

Abstract

When 1-(ω-azidoalkyl)-2-(2,2-dihalovinyl)arenes were heated in DMF, the intramolecular Huisgen cycloaddition of an azido group with a 1,1-dihalovinyl group afforded 5-halo-1,2,3-triazole-fused tricyclic benzo compounds. Based on the remaining bromo groups, carbon elongation by the Mizoroki–Heck or Suzuki–Miyaura coupling reactions, followed by an intramolecular Friedel–Crafts reaction, afforded polycyclic compounds with fused triazole rings. Thereafter, the bromo groups were converted into 2-nitrophenyl groups via the Suzuki–Miyaura coupling reaction, which was followed by the Cadogan reaction; a fluorescent pentacyclic compound was obtained.

Related Literature

Inclusion behavior of water-soluble thiacalix- and calix[4]arenes towards substituted benzenes in aqueous solution

Noriyoshi Kon, Nobuhiko Iki, Sotaro Miyano

2003-01-28 Paper

DOI: 10.1039/B210198J

Direct synthesis of indenes via a rhodium-catalyzed multicomponent Csp2–H annulation reaction

Pierre Querard, Chao-Jun Li

2018-10-15 Communication

DOI: 10.1039/C8OB02359J

Catalyst-free 1 : 2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines

K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, V. M. Muzalevskiy, V. G. Nenajdenko, B. A. Trofimov

2018-10-12 Communication

DOI: 10.1039/C8OB02379D

Synthesis and properties of a lysosome-targeting fluorescent ionophore based on coumarins and squaramides

Xiao-Qiao Hong, Xi-Hui Yu, Wen-Hua Chen

2018-10-11 Communication

DOI: 10.1039/C8OB01957F

Synthesis of poly(ethylene glycol)-supported manganese porphyrins: efficient, recoverable and recyclable catalysts for epoxidation of alkenes

Maurizio Benaglia, Tamara Danelli, Gianluca Pozzi

2003-01-02 Communication

DOI: 10.1039/B210985A

Recent advances in the synthesis of azaphenalene alkaloids: first enantioselective approaches

Sílvia Alujas-Burgos, Pau Bayón, Marta Figueredo

2018-08-03 Review Article

DOI: 10.1039/C8OB01443D

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

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 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.