One-Pot AgOAc-Mediated Synthesis of Polysubstituted Pyrroles from Primary Amines and Aldehydes: Application to the Total Synthesis of Purpurone

被引：105

作者：

Li, Qingjiang ^{[1
]}

Fan, Aili ^{[1
]}

Lu, Zhiyao ^{[1
]}

Cui, Yuxin ^{[1
]}

Lin, Wenhan ^{[1
]}

Jia, Yanxing ^{[1
,2
]}

机构：

[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 18期

基金：

中国国家自然科学基金;

关键词：

EFFICIENT TOTAL-SYNTHESIS; C BOND FORMATION; LEAD-TETRAACETATE; ENAMINE-ESTERS; SUBSTITUTED PYRROLES; SEQUENTIAL REACTIONS; DIRECT ANNULATION; ALPHA-ARYLATION; OXIDATION; ALKALOIDS;

D O I：

10.1021/ol101644g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method for the synthesis of 1,3,4-trisubstituted or 3,4-disubstituted pyrroles has been developed. The reaction represents the first time that pyrroles are synthesized directly from readily available aldehydes and amines (anilines) as starting materials. This method has been successfully applied to the rapid synthesis of purpurone.

引用

页码：4066 / 4069

页数：4

共 50 条

[41] Metal-Free Synthesis of Polysubstituted Pyrroles by (Diacetoxyiodo)Benzene-Mediated Cascade Reaction of 3-Alkynyl Amines [J].

Mo, Dong-Liang ;

Ding, Chang-Hua ;

Dai, Li-Xin ;

Hou, Xue-Long .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (12) :3200-3204

[42] One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides [J].

Alom, Nur-E ;

Wu, Fan ;

Li, Wei .

ORGANIC LETTERS, 2017, 19 (04) :930-933

[43] One-pot synthesis of imides from anhydrides in solid phase [J].

Taherpour, Avat Arman ;

Abramian, Araz ;

Kardanyazd, Haniyeh .

ASIAN JOURNAL OF CHEMISTRY, 2006, 18 (03) :2401-2403

[44] A simple one-pot synthesis of β-alkoxy alcohols from alkenes [J].

Le Bras, J ;

Chatterjee, D ;

Muzart, J .

TETRAHEDRON LETTERS, 2005, 46 (28) :4741-4743

[45] One-pot chemoenzymatic synthesis of glycolic acid from formaldehyde [J].

Li, Tianzhen ;

Tan, Zijian ;

Tang, Zijing ;

Liu, Pi ;

Liu, Haifeng ;

Zhu, Leilei ;

Ma, Yanhe .

GREEN CHEMISTRY, 2022, 24 (13) :5064-5069

[46] Catalyst-free facile and efficient one-pot synthesis of densely functionalized pyrroles and α-amino ketones [J].

Vanga, Sivarama Krishna Reddy ;

Bollikolla, Hari Babu ;

Peruri, V. V. Satyanarayana .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (03) :892-899

[47] Chemoselective one-pot synthesis of β-keto sulfones from ketones [J].

Rawat, Vikas S. ;

Reddy, Perla L. M. ;

Sreedhar, Bojja .

RSC ADVANCES, 2014, 4 (10) :5165-5168

[48] Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light [J].

Gambuti, Francesco ;

Pizzorno, Jacopo ;

Lambruschini, Chiara ;

Riva, Renata ;

Moni, Lisa .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 :2722-2731

[49] Laccase Mediated One-Pot, Green Synthesis of Thiazoles, β-Keto Sulfones and Imidazopyridines [J].

Gaikwad, Sanjay S. ;

Hiwale, Mehul M. ;

Zyate, Shankesh C. ;

Gaikwad, Santosh B. ;

Waghmode, Suresh B. ;

Jadhao, Amardeep R. .

APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 2025, 197 (04) :2757-2767

[50] One-Pot Three-Component Synthesis of 4(3H)-Quinazolinones from Benzyl Halides, Isatoic Anhydride, and Primary Amines [J].

Adib, Mehdi ;

Sheikhi, Ehsan ;

Bijanzadeh, Hamid Reza .

SYNLETT, 2012, 23 (01) :85-88

← 1 2 3 4 5 →