Synthesis and resolution of 2-amino-5-aza[6]helicene

被引:3
作者
Bhalodi, Esha H. [1 ]
Patel, Krupa N. [1 ]
Bedekar, Ashutosh, V [1 ]
机构
[1] Maharaja Sayajirao Univ Baroda, Fac Sci, Dept Chem, Vadodara 390002, India
关键词
Aza[6]helicene; CD analysis; Helical isomers; Single crystal analysis; ONE HUNDRED YEARS; STEREOSELECTIVE SYNTHESES; CHIRAL RECOGNITION; CRYSTAL-STRUCTURES; SMALL MOLECULES; PART; CARBAZOLE; HELICENE; DERIVATIVES; PHOTOCYCLIZATION;
D O I
10.1016/j.tet.2022.132761
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 2-amino-5-aza[6]helicene and its derivatives is reported. The diastereomeric (R)menthylcarbamate derivative of this aza[6]helicene is prepared and its isomers were physically separated by column chromatography and their optical properties were measured. Optically pure isomer (P)2-amino-5-aza[6]helicene was generated and its Boc-derivative was prepared.(c) 2022 Elsevier Ltd. All rights reserved.
引用
收藏
页数:7
相关论文
共 50 条
[31]   Formation of a trithia[5]helicene in an unexpected photoreaction of a methyl-substituted bis(dithienylethenyl)thiophene through a double sequence of 6π-electrocyclization/aromatization (dehydrogenation/demethylation) [J].
Yamamoto, Atsushi ;
Matsui, Yasunori ;
Ohta, Eisuke ;
Ogaki, Takuya ;
Sato, Hiroyasu ;
Furuyama, Taniyuki ;
Kobayashi, Nagao ;
Mizuno, Kazuhiko ;
Ikeda, Hiroshi .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2016, 331 :48-55
[32]   Synthesis and Structural Properties of Aza[n]helicene Platinum Complexes: Control of Cis and Trans Stereochemistry [J].
Mendola, Daniele ;
Saleh, Nidal ;
Hellou, Nora ;
Vanthuyne, Nicolas ;
Roussel, Christian ;
Toupet, Loic ;
Castiglione, Franca ;
Melone, Federica ;
Caronna, Tullio ;
Fontana, Francesca ;
Marti-Rujas, Javier ;
Parisini, Emilio ;
Malpezzi, Luciana ;
Mele, Andrea ;
Crassous, Jeanne .
INORGANIC CHEMISTRY, 2016, 55 (05) :2009-2017
[33]   Synthesis, Structures, Resolution, and Chiroptical Properties of 1,16-Diaryl-Substituted Benzo[5] helicene Derivatives [J].
Lin, Wei-Bin ;
Li, Meng ;
Fang, Lei ;
Shen, Yun ;
Chen, Chuan-Feng .
CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (01) :86-94
[34]   2,13-Diaza[5]helicene: synthesis, theoretical calculations and spectroscopic properties [J].
Caronna, Tullio ;
Fontana, Francesca ;
Longhi, Giovanna ;
Mele, Andrea ;
Natali Sora, Isabella ;
Vigano, Luca .
ARKIVOC, 2009, :145-155
[35]   Enantioselective Helicene Synthesis by Rhodium-Catalyzed [2+2+2] Cycloaddition [J].
Tanaka, Ken ;
Morita, Futo .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2022, 80 (11) :1019-1027
[36]   A Combined Experimental and Theoretical Study on the Stereodynamics of Monoaza[5]helicenes: Solvent-Induced Increase of the Enantiomerization Barrier in 1-Aza-[5]helicene [J].
Caronna, Tullio ;
Mele, Andrea ;
Famulari, Antonino ;
Mendola, Daniele ;
Fontana, Francesca ;
Juza, Markus ;
Kamuf, Matthias ;
Zawatzky, Kerstin ;
Trapp, Oliver .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (40) :13919-13924
[37]   Enantioselective Helicene Synthesis by Rhodium-Catalyzed [2+2+2] Cycloadditions [J].
Tanaka, Ken ;
Kimura, Yuki ;
Murayama, Koichi .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) :375-385
[38]   Rational Design and Synthesis of [5] Helicene-Derived Phosphine Ligands and Their Application in Pd-Catalyzed Asymmetric Reactions [J].
Yamamoto, Kosuke ;
Shimizu, Takashi ;
Igawa, Kazunobu ;
Tomooka, Katsuhiko ;
Hirai, Go ;
Suemune, Hiroshi ;
Usui, Kazuteru .
SCIENTIFIC REPORTS, 2016, 6
[39]   A [2+2+2] cyclization strategy for the synthesis of phosphorus embedding [6]helicene-like structures [J].
Aillard, Paul ;
Retailleau, Pascal ;
Voituriez, Arnaud ;
Marinetti, Angela .
CHEMICAL COMMUNICATIONS, 2014, 50 (17) :2199-2201
[40]   Synthesis and study of the structural properties of oxa[5]helicene derivatives [J].
Sundar, M. Shyam ;
Sahoo, Sibaprasad ;
Bedekar, Ashutosh V. .
TETRAHEDRON-ASYMMETRY, 2016, 27 (16) :777-781