Synthesis of spirocyclopropanes via iodine-promoted bimolecular cyclization of 2-benzylidene 1,3-indandiones

被引：0

作者：

He, Zeng-Yang ^{[1
]}

Ning, Yong ^{[1
]}

Zhao, Yu-Fei ^{[3
]}

Diao, Hong-Lin ^{[1
]}

Zou, Peng ^{[1
]}

Wang, Wen-Bin ^{[1
]}

Shu, Jun-Sheng ^{[1
]}

Xu, Hui ^{[2
]}

机构：

[1] China Tobacco Anhui Ind Co Ltd, Technol Ctr, Hefei 230088, Anhui, Peoples R China

[2] Anhui Polytech Univ, Sch Chem & Environm Engn, Wuhu 241000, Anhui, Peoples R China

[3] China Tobacco Anhui Ind Co Ltd, Mkt Ctr, Hefei, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2022年 / 52卷 / 24期

关键词：

Benzylidene indandiones; bimolecular cyclization; iodine; spirocyclopropanes; ENANTIOSELECTIVE SYNTHESIS; ALKYLIDENE OXINDOLES; MOLECULAR-IODINE; MICHAEL ADDITION; CYCLOPROPANES; SPIROOXINDOLES; HETEROCYCLES; DERIVATIVES; COMPOUND;

D O I：

10.1080/00397911.2022.2146513

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient iodine-promoted bimolecular annulation of 2-benzylidene 1,3-indandiones has been developed. Following this protocol, a series of spirocyclopropane derivatives were furnished in good to excellent yields. The present protocol features mild conditions, short reaction time, high efficiency, good chemoselectivity and remarkable functional group tolerance.

引用

页码：2322 / 2333

页数：12

共 37 条

[21] Synthesis of Indolo[2,1-a ]isoquinolines via Copper-Catalyzed C-C Coupling and Cyclization of 2-(2-Bromoaryl)-1 H -indoles with 1,3-Diketones
Lee, Ha Kyeong
Pham Duy Quang Dao
Kim, Young-su
Cho, Chan Sik
SYNTHESIS-STUTTGART, 2018, 50 (16): : 3243 - 3249
[22] Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-lodo-1H-indenes
Murai, Masahito
Takai, Kazuhiko
ORGANIC LETTERS, 2019, 21 (17) : 6756 - 6760
[23] Synthesis of 2-Carbonylimidazo[1,2-a] pyridines via Iodine-mediated Intramolecular Cyclization of 2-Amino-N-propargylpyridinium Bromides
Pandey, Khima
Kaswan, Pinku
Saroj
Kumar, Anil
CHEMISTRYSELECT, 2016, 1 (21): : 6669 - 6672
[24] Three-component synthesis of substituted β-(trifluoromethyl)pyrroles via Grob cyclization of 1,1,1-trifluoro-3-nitrobut-2-ene with 1,3-dicarbonylic compounds and ammonia or primary amines
Korotaev, Vladislav Yu.
Barkov, Alexey Yu.
Kotovich, Ivan V.
Sosnovskikh, Vyacheslav Ya.
JOURNAL OF FLUORINE CHEMISTRY, 2012, 138 : 42 - 47
[25] Asymmetric synthesis of spiro-structural 2,3-dihydrobenzofurans via the bifunctional phosphonium salt-promoted [4+1] cyclization of ortho-quinone methides with α-bromoketones
Zhang, Song
Yu, Xiaojun
Pan, Jianke
Jiang, Chunhui
Zhang, Hongsu
Wang, Tianli
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (22) : 3799 - 3803
[26] One-Pot Synthesis of 1H-Indazole-4,7-diols via Iodine(III)-Mediated [3+2] Cyclization in Water
Hou, Yingwei
Cai, Chao
Yu, Guangli
SYNLETT, 2016, 27 (05) : 773 - 776
[27] Molecular Iodine-Promoted Transimination for the Synthesis of 6-Phenylpyrido[2,1:2,3]imidazo[4,5-c]quinoline and 6-(Pyridin-2-yl)pyrido[2,1:2,3]imidazo[4,5-c]quinolines
Sunkari, Satish
Shaik, Siddiq Pasha
Krishna, Namballa Hari
Rao, Ayanampudi Venkata Subba
Kodiripaka, Bheeshma Geetanjali
Alarifi, Abdullah
Kamal, Ahmed
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (12) : 1830 - 1837
[28] Highly Z-selective synthesis of 1,3-oxathiol-2-ylidenes and 4-methylene-oxazolidine-2-thiones via atom-specific 5-exo-dig cyclization of propargyl alcohol with isothiocyanate
Savarimuthu, S. Antony
Prakash, D. G. Leo
Thomas, S. Augustine
Gandhi, Thirumanavelan
Bera, Mrinal K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (18) : 3552 - 3562
[29] Molecular iodine mediated oxidative cross-coupling of sp3 C-H with sp2 C-H: direct synthesis of substituted indolo[2,3-b]carbazoles via formal [2+2+1+1] cyclization
Xue, Wei-jian
Gao, Qing-He
Wu, An-xin
TETRAHEDRON LETTERS, 2015, 56 (51) : 7115 - 7119
[30] Direct Synthesis of Sulfinylated Benzofulvenes via BF3•Et2O-Promoted Cascade Reactions of Arylsulfinic Acids with 1,3-Enynes
Zhang, Zhen
Li, Anni
Zhao, Beibei
Li, Pinhua
Wang, Lei
Miao, Tao
ORGANIC LETTERS, 2021, 23 (21) : 8204 - 8208

← 1 2 3 4 →