Substrate-controlled divergent synthesis of polycyclic indoloazepines and indolodiazepines via 1,5-hydride shift/7-cyclization cascades

被引：55

作者：

Liu, Siyuan ^{[1
]}

Qu, Jingping ^{[1
]}

Wang, Baomin ^{[1
]}

机构：

[1] Dalian Univ Technol, Sch Pharmaceut Sci & Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 57期

关键词：

PSYCHOPHARMACOLOGICAL TREATMENT; BOND FUNCTIONALIZATION; BIPOLAR DISORDER; CONSTRUCTION; TANDEM; SEQUENCE; ANALOGS;

D O I：

10.1039/c8cc03804j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel and practical acid-catalyzed cyclization of 2-indolyl aryl carbinols via tandem dehydration/1,5-hydride shift/7-cyclization sequences has been developed. By appropriate variation of the substrate, diverse polycyclic-fused indoles were synthesized in good yield, thus demonstrating the high efficiency, transition-metal-free nature, and high step/atom economy of the synthesis strategy.

引用

页码：7928 / 7931

页数：4

共 37 条

[1] Synthesis and biological activity of fused tetracyclic Pyrrolo[2,1-c][1,4] benzodiazepines [J].

Annor-Gyamfi, Joel K. ;

Jarrett, John M. ;

Osazee, Joseph O. ;

Bialonska, Dobrusia ;

Whitted, Crystal ;

Palau, Victoria E. ;

Shilabin, Abbas G. .

HELIYON, 2018, 4 (02)

[2]

[Anonymous], J PHARM POLICY PRACT

[3] Trends in the psychopharmacological treatment of bipolar disorder: a nationwide register-based study [J].

Bjorklund, Louise ;

Horsdal, Henriette Thisted ;

Mors, Ole ;

Ostergaard, Soren Dinesen ;

Gasse, Christiane .

ACTA NEUROPSYCHIATRICA, 2016, 28 (02) :75-84

[4] Utilization of Psychopharmacological Treatment Among Patients With Newly Diagnosed Bipolar Disorder From 2001 to 2010 [J].

Chang, Chia-Ming ;

Wu, Chi-Shin ;

Huang, Ya-Wen ;

Chau, Yeuk-Lun ;

Tsai, Hui-Ju .

JOURNAL OF CLINICAL PSYCHOPHARMACOLOGY, 2016, 36 (01) :32-44

[5] Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization [J].

Chang, Yong-Zhi ;

Li, Ming-Lei ;

Zhao, Wen-Feng ;

Wen, Xiaoan ;

Sun, Hongbin ;

Xu, Qing-Long .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19) :9620-9627

[6] Benzodiazepines: An Old Class of New Antihypertensive Drugs? [J].

Colussi, GianLuca ;

Catena, Cristiana ;

Darsie, Daniele ;

Sechi, Leonardo Alberto .

AMERICAN JOURNAL OF HYPERTENSION, 2018, 31 (04) :402-404

[7] Synthesis of azepino[3,4b]indoles via the Plancher rearrangement [J].

Eisenbeis, Shane A. ;

Phillips, James R. ;

Rescek, Diane ;

Oyola-Cintron, Yatsandra .

TETRAHEDRON LETTERS, 2010, 51 (33) :4303-4305

[8] Dopamine/serotonin receptor ligands.: 13:: Homologization of a benzindoloazecine-type dopamine receptor antagonist modulates the affinities for dopamine D1-D5 receptors [J].

Enzensperger, Christoph ;

Lehmann, Jochen .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (21) :6408-6411

[9] Structure and Reactivity of Indolylmethylium Ions: Scope and Limitations in Synthetic Applications [J].

Follet, Elsa ;

Berionni, Guillaume ;

Mayer, Peter ;

Mayr, Herbert .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17) :8643-8656

[10] Redox-Neutral Indole Annulation Cascades [J].

Haibach, Michael C. ;

Deb, Indubhusan ;

De, Chandra Kanta ;

Seidel, Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2100-2103

← 1 2 3 4 →