Acid-Promoted Cyclization of α-Azidobenzyl Ketones through C═N Bond Formation : Synthesis of 6-Substituted Quinoline Derivatives
An acid-promoted cyclization of α-azidobenzyl ketones has been developed for the synthesis of 6-substituted quinoline derivatives. A variety of synthetically useful 6-OTf or -OMs quinoline derivatives were obtained in moderate to good yields. The reaction proceeds via C═N bond formation without organophosphine, providing convenient access to structurally interesting and synthetically important 6-substituted quinoline derivatives in moderate to good yields. A mechanistic perspective that is different from the traditional intramolecular Schmidt reaction has been proposed.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
|---|---|
| Enthalten in: |
Organic letters - 26(2024), 3 vom: 26. Jan., Seite 586-590 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Zheng, Jing-Yun [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
|---|
| Anmerkungen: |
Date Revised 26.01.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
|---|
| doi: |
10.1021/acs.orglett.3c03697 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM366893327 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM366893327 | ||
| 003 | DE-627 | ||
| 005 | 20240126232122.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240114s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1021/acs.orglett.3c03697 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1271.xml |
| 035 | |a (DE-627)NLM366893327 | ||
| 035 | |a (NLM)38198745 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Zheng, Jing-Yun |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Acid-Promoted Cyclization of α-Azidobenzyl Ketones through C═N Bond Formation |b Synthesis of 6-Substituted Quinoline Derivatives |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Revised 26.01.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a An acid-promoted cyclization of α-azidobenzyl ketones has been developed for the synthesis of 6-substituted quinoline derivatives. A variety of synthetically useful 6-OTf or -OMs quinoline derivatives were obtained in moderate to good yields. The reaction proceeds via C═N bond formation without organophosphine, providing convenient access to structurally interesting and synthetically important 6-substituted quinoline derivatives in moderate to good yields. A mechanistic perspective that is different from the traditional intramolecular Schmidt reaction has been proposed | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Luo, Ying |e verfasserin |4 aut | |
| 700 | 1 | |a Ou, Ting-Ting |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Xin-Jie |e verfasserin |4 aut | |
| 700 | 1 | |a Lao, Yong-Qiang |e verfasserin |4 aut | |
| 700 | 1 | |a Feng, Na |e verfasserin |4 aut | |
| 700 | 1 | |a Peng, Jin-Bao |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Xiang-Zhi |e verfasserin |4 aut | |
| 700 | 1 | |a Yao, Xiaojun |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Ai-Jun |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Organic letters |d 1999 |g 26(2024), 3 vom: 26. Jan., Seite 586-590 |w (DE-627)NLM106817639 |x 1523-7052 |7 nnns |
| 773 | 1 | 8 | |g volume:26 |g year:2024 |g number:3 |g day:26 |g month:01 |g pages:586-590 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1021/acs.orglett.3c03697 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 26 |j 2024 |e 3 |b 26 |c 01 |h 586-590 | ||