Aldehydes Switch Regioselectivity: a Prins Cyclization Strategy for the Synthesis of Indoline-fused THFs and Indole-fused Oxepanes

被引：2

作者：

Chen Xiaobei ^{[1
,2
]}

Jiang Yuanrui ^{[3
,4
]}

Geng Huihui ^{[1
,2
]}

Liu Xingyu ^{[1
,2
]}

Huang Yizhuo ^{[1
,2
]}

Lu Jingwei ^{[1
,2
]}

Gao Chenjing ^{[1
,2
]}

Zhang Shilei ^{[3
,4
]}

Zhang Jian ^{[5
]}

Wang Wei ^{[1
,2
,6
,7
]}

机构：

[1] East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Sch Pharm, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China

[3] Soochow Univ, Jiangsu Key Lab Neuropsychiat Dis, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China

[4] Soochow Univ, Coll Pharmaceut Sci, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China

[5] Shanghai Jiao Tong Univ, Key Lab Cell Differentiat & Apoptosis, Chinese Minist Educ, Clin & Fundamental Res Ctr,Renji Hosp,Sch Med, Shanghai 200025, Peoples R China

[6] Univ Arizona, Dept Pharmacol & Toxicol, 1703 E Mabel St,POB 210207, Tucson, AZ 85721 USA

[7] Univ Arizona, BIO5 Inst, 1703 E Mabel St,POB 210207, Tucson, AZ 85721 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 13期

基金：

中国国家自然科学基金;

关键词：

Prins cyclization; tetrahydrofuran; oxepane; aldehyde; rearrangement; ONE-POT SYNTHESIS; 2,3,5-TRISUBSTITUTED TETRAHYDROFURANS; SUBSTITUTED TETRAHYDROFURANS; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; FACILE; CONSTRUCTION; REAGENTS; ALCOHOLS; CATALYST;

D O I：

10.1002/adsc.202000100

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We have identified a switchable Prins cyclization process to form indoline-fused tetrahydrofurans and indole-fused oxepanes by applying different types of aldehydes under two sets of optimized conditions. Significantly, a novel Prins reaction mechanism involving an oxonium-mediated rearrangement in the formation of five-membered cyclic ethers is realized for the first time.

引用

页码：2620 / 2625

页数：6

共 14 条

[1] Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds
Rapelli, Chandrashekhar
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Subba Reddy, B.V. (basireddy@iict.res.in), 1600, Royal Society of Chemistry (18): : 6710 - 6715
[2] Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds
Rapelli, Chandrashekhar
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (34) : 6710 - 6715
[3] Synthesis of Indole-Fused 1,4-Diazepinones via Photoredox-Catalyzed Cascade Cyclization Reaction
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[5] Synthesis of Indoline-Fused 2,5-Diketopiperazine Scaffolds via Ugi-4CR in the Basic Mediated Tandem Consecutive Cyclization
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[6] Regioselective Synthesis of Indole-Fused Seven-Membered N-Heterocycles via Photoredox-Catalyzed Intramolecular Cyclization
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[7] Synthesis of Indole-Fused Dihydrothiopyrano Scaffolds via (3+3)- Annulations of Donor-Acceptor Cyclopropanes with Indoline-2-Thiones
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[8] Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds (vol 18, pg 6710, 2020)
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[10] Sequential hydroarylation/Prins cyclization: an efficient strategy for the synthesis of angularly fused tetrahydro-2H-pyrano[3,4-c]quinolines
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