Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls

被引：18

作者：

Wani, Imtiyaz Ahmad ^{[1
,2
]}

Das, Subhomoy ^{[1
]}

Mondal, Shobhan ^{[1
]}

Ghorai, Manas K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] Amar Singh Coll, Dept Chem, Srinagar 190008, Jammu & Kashmir, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 23期

关键词：

ADDITION-CYCLIZATION REACTIONS; ACTIVATED AZIRIDINES; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; SYNTHETIC ROUTE; CATALYSIS; INDOLES; DERIVATIVES; POTENT; (1H-INDOL-2-YL)METHANOLS;

D O I：

10.1021/acs.joc.8b02339

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%)via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF3 center dot OEt2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-detosylation cascade.

引用

页码：14553 / 14567

页数：15

共 3 条

[1] A synthetic route to 1,4-disubstituted tetrahydro-β-carbolines and tetrahydropyranoindoles via ring-opening/Pictet-Spengler reaction of aziridines and epoxides with indoles/aldehydes
Wani, Imtiyaz Ahmad
Goswami, Gaurav
Sk, Sahid
Mal, Abhijit
Sayyad, Masthanvati
Ghorai, Manas K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (02) : 272 - 287
[2] Construction of 4-spiroannulated tetrahydroisoquinoline skeletons via a sequential ring opening of aziridines and Pictet-Spengler reaction
Xing, Siyang
Wang, Chenyu
Gao, Tingxuan
Wang, Yuhan
Wang, Hongzheng
Wang, Hanfei
Wang, Kui
Zhu, Bolin
NEW JOURNAL OF CHEMISTRY, 2022, 46 (05) : 2553 - 2558
[3] Stereoselective Syntheses of Highly Functionalized Imidazolidines and Oxazolidines via Ring-Opening Cyclization of Activated Aziridines and Epoxides with Amines and Aldehydes
Tarannum, Saima
Sk, Sahid
Das, Subhomoy
Wani, Imtiyaz Ahmad
Ghorai, Manas K.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02) : 367 - 379

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