Hydrazone Radical Promoted Vicinal Difunctionalization of Alkenes and Trifunctionalization of Allyls: Synthesis of Pyrazolines and Tetrahydropyridazines

被引:86
作者
Duan, Xiao-Yong [1 ]
Yang, Xiu-Long [1 ]
Fang, Ran [1 ]
Peng, Xie-Xue [1 ]
Yu, Wei [1 ]
Han, Bing [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND-DISSOCIATION ENTHALPIES; AEROBIC OXIDATIVE SYNTHESIS; METAL-FREE; NITROGEN RADICALS; CYCLIZATION; DIOXYGENATION; DIAMINATION; EFFICIENT; OXIMES; AMIDYL;
D O I
10.1021/jo4016908
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intramolecular addition of hydrazone radicals to carbon-carbon double bonds was achieved by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or DIAD (diisopropyl azodicarboxylate) as the hydrazone radical initiator as well as the carbon radical scavenger. Consequently, alkenes were difunctionalized to afford pyrazolines and tetrahydropyridazines via C-N forming S-exo-trig and 6-exo-trig cyclizations, respectively, and allyls were trifunctionalized to afford pyrazolines via C-N forming tandem 1,5-H-shift/S-exo-trig cyclizations under metal-free neutral conditions.
引用
收藏
页码:10692 / 10704
页数:13
相关论文
共 62 条
[1]   Zinc-catalyzed synthesis of pyrazolines and pyrazoles via hydrohydrazination [J].
Alex, Karolin ;
Tillack, Annegret ;
Schwarz, Nicolle ;
Beller, Matthias .
ORGANIC LETTERS, 2008, 10 (12) :2377-2379
[2]   Stereospecific Intramolecular C-H Amination of 1-Aza-2-azoniaallene Salts [J].
Bercovici, Daniel A. ;
Brewer, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (24) :9890-9893
[3]   DI TERT BUTYLIMINOXY, A FREE RADICAL OF MODERATE STABILITY [J].
BROKENSHIRE, JL ;
MENDENHALL, GD ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (20) :5278-+
[4]   Gold(I)-Catalyzed Formation of 3-Pyrazolines through Cycloaddition of Diaziridine to Alkynes [J].
Capretto, David A. ;
Brouwer, Chad ;
Poor, Catherine B. ;
He, Chuan .
ORGANIC LETTERS, 2011, 13 (21) :5842-5845
[5]   Characterization of Cytochrome P450-Mediated Bioactivation of a Compound Containing the Chemical Scaffold, 4,5-Dihydropyrazole-1-carboxylic acid-(4-chlorophenyl amide), to a Chemically Reactive p-Chlorophenyl Isocyanate Intermediate in Human Liver Microsomes [J].
Chen, Hao ;
Zientek, Michael ;
Jalaie, Mehran ;
Zhang, Yanhua ;
Bigge, Christopher ;
Mutlib, Abdul .
CHEMICAL RESEARCH IN TOXICOLOGY, 2009, 22 (09) :1603-1612
[6]   Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO [J].
Chen, Yong-Xing ;
Qian, Ling-Feng ;
Zhang, Wei ;
Han, Bing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) :9330-9333
[7]   O-H bond dissociation enthalpies of oximes: A theoretical assessment and experimental implications [J].
Chong, Sha-Sha ;
Fu, Yao ;
Liu, Lei ;
Guo, Qing-Xiang .
JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (50) :13112-13125
[8]   Novel pyrazole derivatives: Synthesis and evaluation of anti-angiogenic activity [J].
Christodoulou, Michael S. ;
Liekens, Sandra ;
Kasiotis, Konstantinos M. ;
Haroutounian, Serkos A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (12) :4338-4350
[9]   Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation [J].
Du, Haifeng ;
Zhao, Baoguo ;
Shi, Yian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8590-+
[10]   THE GENERATION OF NITROGEN RADICALS AND THEIR CYCLIZATIONS FOR THE CONSTRUCTION OF THE PYRROLIDINE NUCLEUS [J].
ESKER, JL ;
NEWCOMB, M .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 58, 1993, 58 :1-45