Synthesis of cyclobutyl-fused tetralones via photolytic [2+2] Cycloaddition

被引：0

作者：

Hsueh, Nai-Chen ^{[1
]}

Chen, Pin-Hsien ^{[1
]}

Chang, Meng-Yang ^{[1
,2
,3
]}

机构：

[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan

[2] Kaohsiung Med Univ Hosp, Dept Med Res, Kaohsiung 807, Taiwan

[3] Natl Pingtung Univ Sci & Technol, NPUST Coll Profess Studies, Pingtung 912, Taiwan

来源：

TETRAHEDRON | 2023年 / 143卷

关键词：

Cyclobutyl-fused; 1-tetralones; o-Cinnamyl acetophenones; Arylaldehydes; Photolytic annulation; o-Cinnamyl chalcones; DRUG DISCOVERY; DERIVATIVES; OXETANES;

D O I：

10.1016/j.tet.2023.133552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we demonstrate an efficient two-step preparation of substituted cyclobutyl-fused 1-tetralones bearing four contiguous stereochemical centers, including (i) intermolecular aldol condensation of o-cinnamyl acetophenones with arylaldehydes, and (ii) intramolecular photolytic annulation of the resulting o-cinnamyl chalcones. The key structures are determined by single-crystal X-ray analysis. Plausible mechanism is also presented.

引用

页数：10

共 50 条

[31] Redox-induced reversible [2+2] cycloaddition of an etheno-fused diporphyrin
Miyagawa, Kazuya
Hisaki, Ichiro
Fukui, Norihito
Shinokubo, Hiroshi
[J]. CHEMICAL SCIENCE, 2021, 12 (14) : 5224 - 5229
[32] SYNTHESIS OF HETEROCYCLES BY THERMAL (2+2)-CYCLOADDITION REACTIONS OF ACETYLENES
REINHOUDT, DN
[J]. BULLETIN DES SOCIETES CHIMIQUES BELGES, 1981, 90 (06): : 633 - 643
[33] Equilibration of the [2+2] Cycloaddition of Silyl Enol Ethers Catalyzed by Ethylaluminium Dichloride: Diastereoselectivity Switch in the Synthesis of Fused Cyclobutanes
Hata, Kenji
Arichi, Norihito
Yamaoka, Yousuke
Yamada, Ken-ichi
Takemoto, Yoshiji
Takasu, Kiyosei
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (06) : 706 - 710
[34] Stereoselective Construction of Highly Functionalized Azetidines via a [2+2]-Cycloaddition
Ye, Yang
Wang, Hua
Fan, Renhua
[J]. ORGANIC LETTERS, 2010, 12 (12) : 2802 - 2805
[35] Functionalized cyclobutenes via multicomponent thermal [2+2] cycloaddition reactions
Sheldrake, HM
Wallace, TW
Wilson, CP
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4233 - 4236
[36] FORMATION OF TRICYCLIC THIETANE DERIVATIVES VIA INTRAMOLECULAR (2+2) CYCLOADDITION
WIPF, P
HEIMGARTNER, H
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (04) : 992 - 994
[37] Crack healing in polymeric materials via photochemical [2+2] cycloaddition
Chung, CM
Roh, YS
Cho, SY
Kim, JG
[J]. CHEMISTRY OF MATERIALS, 2004, 16 (21) : 3982 - +
[38] Regioselective synthesis of 1,2-diarylbenzazetidenes via [2+2] cycloaddition reactions of benzyne with azomethines
Singal, KK
Kaur, J
[J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (18) : 2809 - 2815
[39] Catalytic Asymmetric Synthesis of Stable Oxetenes via Lewis Acid-Promoted [2+2] Cycloaddition
Aikawa, Kohsuke
Hioki, Yuta
Shimizu, Natsumi
Mikami, Koichi
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) : 20092 - 20095
[40] Synthesis of Oxygenated ortho-Methylbenzaldehydes via Aryne [2+2] Cycloaddition and Benzocyclobutenol Ring Opening
Maturi, Mark M.
Ohmori, Ken
Suzuki, Keisuke
[J]. CHIMIA, 2018, 72 (12) : 870 - 873

← 1 2 3 4 5 →