Lewis Acid Mediated Intramolecular C-C Bond Formation of Alkyne-Epoxide Leading to Six-Membered Nitrogen and Oxygen Heterocycles

被引：20

作者：

Ghosh, Priya ^{[1
]}

Saha, Pipas ^{[1
]}

Bondalapati, Somasekhar ^{[1
]}

Indukuri, Kiran ^{[1
]}

Saikia, Anil K. ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 09期

关键词：

STEREOSELECTIVE-SYNTHESIS; CROSS-CYCLIZATION; FACILE SYNTHESIS; PRINS REACTION; BREVETOXIN-B; AZA-PRINS; DERIVATIVES; ENYNES; CARBOCYCLIZATION; CYCLOADDITIONS;

D O I：

10.1021/jo402550e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular C-C bond formation of oxygen- and nitrogen-tethered alkynes and epoxide mediated by Lewis acid under ambient conditions is described. A simple procedure for the synthesis of 3,6- and 5,6-dihydropyrans and 3,4-dehydropiperidines from acyclic building blocks in good yields without using any transition metal is shown.

引用

页码：4119 / 4124

页数：6

共 50 条

[31] Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)-H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds
Mita, Tsuyoshi
Uchiyama, Masashi
Sato, Yoshihiro
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (06) : 1275 - 1280
[32] Stereoelectronic Interactions Exhibited by 1JC-H One-Bond Coupling Constants and Examination of the Possible Existence of the Intramolecular α-Effect in Six-Membered Oxygen-Containing Heterocycles
Juaristi, Eusebio
Notario, Rafael
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (06): : 3293 - 3298
[33] Silver-Mediated Radical Cyclization of Alkynoates and α-Keto Acids Leading to Coumarins via Cascade Double C-C Bond Formation
Yan, Kelu
Yang, Daoshan
Wei, Wei
Wang, Fen
Shuai, Yuanyuan
Li, Qiannan
Wang, Hua
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1550 - 1556
[34] Copper(II) Acetate/Oxygen-Mediated Nucleophilic Addition and Intramolecular C-H Activation/C-N or C-C Bond Formation: One-Pot Synthesis of Benzimidazoles or Quinazolines
He, Hua-Feng
Wang, Zhi-Jing
Bao, Weiliang
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 2905 - 2912
[35] Synthesis of a coronene analogue containing an amide bond by Pd-mediated intramolecular C-C bond formation of 2-halogenated 4-(alkylamino)benzoic acid cyclic trimer
Yokoyama, Akihiro
Ishii, Arisa
Ohishi, Tomoyuki
Kikkawa, Shoko
Azumaya, Isao
TETRAHEDRON LETTERS, 2021, 62
[36] Ni-catalyzed C-O bond cleavage of 3-phenoxy acrylic acid derivatives and subsequent intramolecular C-C bond formation to give benzofurans
Shohei, Ohno
Murai, Kenichi
Fujioka, Hiromichi
Arisawa, Mitsuhiro
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[37] HYDROPEROXIDE-MEDIATED C-C BOND FORMATION - SYNTHESIS OF 1,2-DIOXOLANES FROM ALKOXYHYDROPEROXIDES IN THE PRESENCE OF LEWIS-ACIDS
DUSSAULT, PH
ZOPE, U
TETRAHEDRON LETTERS, 1995, 36 (21) : 3655 - 3658
[38] Iron/acetic acid mediated intermolecular tandem C-C and C-N bond formation: an easy access to acridinone and quinoline derivatives
Rajawinslin, R. R.
Gawande, Sachin D.
Kavala, Veerababurao
Huang, Yi-Hsiang
Kuo, Chun-Wei
Kuo, Ting-Shen
Chen, Mei-Ling
He, Chiu-Hui
Yao, Ching-Fa
RSC ADVANCES, 2014, 4 (71) : 37806 - 37811
[39] Iron/acetic acid mediated intermolecular tandem C-C and C-N bond formation: An easy access to acridinone and quinoline derivatives
Yao, Ching-Fa, 1600, Royal Society of Chemistry (40):
[40] Efficient C-C Bond Formation between Two Levulinic Acid Molecules To Produce C10 Compounds with the Cooperation Effect of Lewis and Bronsted Acids
Li, Zheng
Zhang, Jiaojiao
Nielsen, Michael Martin
Wang, Hongliang
Chen, Chunyan
Xu, Junli
Wang, Yingxiong
Deng, Tiansheng
Hou, Xianglin
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (05): : 5708 - 5711

← 1 2 3 4 5 →