One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3-Triazoles and 2-Hydroxymethylallyl Carbonates

被引：2

作者：

Park, Jong-Un ^{[1
]}

Huang, Liang-Zhu ^{[1
,2
]}

Cho, Ho-Jun ^{[1
]}

Park, Boyoung Y. ^{[3
]}

Kim, Ju Hyun ^{[1
]}

机构：

[1] Gyeongsang Natl Univ, Res Inst Nat Sci, Dept Chem BK21 Four, Jinju 52828, South Korea

[2] Yanan Univ, Coll Chem & Chem Engn, Yanan 716000, Shaanxi, Peoples R China

[3] Kyung Hee Univ, Coll Pharm, Seoul 02447, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

HIGHLY SUBSTITUTED PYRROLES; POLYSUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; STEP ECONOMY; THERMAL REARRANGEMENT; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; ATOM ECONOMY; COPPER;

D O I：

10.1021/acs.joc.2c02602

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, tandem one-pot approach to synthesize multisubstituted 2-acylpyrroles from readily prepared N-tosyl triazoles and 2-hydroxymethylallyl carbonates is reported. The reaction proceeds via Rh(II)-catalyzed O-H insertion, [3,3]sigmatropic rearrangement, Pd(0)-catalyzed oxidative addition, intramolecular cyclization, DBU-promoted E1cB elimination, double bond isomerization, and aromatization, enabling the disconnection and formation of multiple bonds in one reactor. The approach represents a highly regioselective way to access di-, tri-, and tetra-substituted NH pyrroles with high efficiency.

引用

页码：585 / 593

页数：9

共 79 条

[1] Pd-Catalyzed asymmetric [5+2] cycloaddition of vinylethylene carbonates and cyclic imines: access to N-fused 1,3-oxazepines [J].

Ahn, Hye-In ;

Park, Jong-Un ;

Xuan, Zi ;

Kim, Ju Hyun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (48) :9826-9830

[2] INTERMEDIATES IN THE PAAL-KNORR SYNTHESIS OF PYRROLES [J].

AMARNATH, V ;

ANTHONY, DC ;

AMARNATH, K ;

VALENTINE, WM ;

WETTERAU, LA ;

GRAHAM, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6924-6931

[3] Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration [J].

Andreou, Dimitrios ;

Kallitsakis, Michael G. ;

Loukopoulos, Edward ;

Gabriel, Catherine ;

Kostakis, George E. ;

Lykakis, Ioannis N. .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :2104-2113

[4] A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans [J].

Antonioletti, R ;

Bovicelli, P ;

Malancona, S .

TETRAHEDRON, 2002, 58 (03) :589-596

[5] THEORETICAL-STUDIES OF THE [1,5] SIGMATROPIC HYDROGEN SHIFT IN CYCLOPENTADIENE, PYRROLE, AND PHOSPHOLE [J].

BACHRACH, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5414-5421

[6] A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].

BARTON, DHR ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100

[7] Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics [J].

Bhardwaj, Varun ;

Gumber, Divya ;

Abbot, Vikrant ;

Dhiman, Saurabh ;

Sharma, Poonam .

RSC ADVANCES, 2015, 5 (20) :15233-15266

[8] Redox Economy in Organic Synthesis [J].

Burns, Noah Z. ;

Baran, Phil S. ;

Hoffmann, Reinhard W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2854-2867

[9] One-Pot Synthesis of N-H-Free Pyrroles from Aldehydes and Alkynes [J].

Chen, Lai ;

Huo, Jing-Qian ;

Si, He-Long ;

Xu, Xin-Yu ;

Kou, Song ;

Mao, Jianyou ;

Zhang, Jin-Lin .

ORGANIC LETTERS, 2021, 23 (11) :4348-4352

[10] Synthesis of multisubstituted pyrroles via a CuI-catalyzed three-component coupling and a 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)/silica-gel promoted cyclization [J].

Chen, Wanli ;

Jin, Lina ;

Zhu, Yinghong ;

Mo, Weimin .

ARKIVOC, 2012, :295-307

← 1 2 3 4 5 6 7 8 →