1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis

被引：8

作者：

Mielgo, Antonia ^{[1
]}

Palomo, Claudio ^{[1
]}

机构：

[1] Univ Basque Country, Dept Quim Organ 1, Fac Quim, Apdo 1072, San Sebastian 20080, Spain

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷

关键词：

asymmetric catalysis; bifunctional catalysts; 1H-imidazol-4(5H)-ones; pronucleophiles; thiazol-4(5H)-ones; CARBON BOND FORMATION; ENANTIOSELECTIVE MICHAEL ADDITION; AMINO-ACID-DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; 1,4-ADDITION REACTION; GAMMA-ADDITION; SOFT ENOLIZATION; THIOUREA ORGANOCATALYSTS; QUATERNARY STEREOCENTERS; BIOLOGICAL EVALUATION;

D O I：

10.3762/bjoc.12.90

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric catalysis represents a very powerful tool for the synthesis of enantiopure compounds. In this context the main focus has been directed not only to the search for new efficient chiral catalysts, but also to the development of efficient pronucleophiles. This review highlights the utility and first examples of 1H-imidazol-4(5H)-ones and thiazol-4(5H)-ones as pronucleophiles in catalytic asymmetric reactions.

引用

页码：918 / 936

页数：19

共 50 条

[1] Catalytic Enantioselective Synthesis of N,C,C-Trisubstituted -Amino Acid Derivatives Using 1H-Imidazol-4(5H)-ones as Key Templates
Etxabe, Julen
Izquierdo, Joseba
Landa, Aitor
Oiarbide, Mikel
Palomo, Claudio
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (23) : 6883 - 6886
[2] Synthesis, anti-diabetic profiling and molecular docking studies of 2-(2-arylidenehydrazinyl)thiazol-4(5H)-ones
Mehmood, Hasnain
Haroon, Muhammad
Akhtar, Tashfeen
Woodward, Simon
Haq, Saadia
Alshehri, Saad M.
FUTURE MEDICINAL CHEMISTRY, 2024, 16 (12) : 1255 - 1266
[3] Nucleophilic rhodanine, thiazolidine-2,4-dione and thiazol-4(5H)-one substrates in asymmetric reactions
Paladhi, Sushovan
Jana, Barnali
Pathak, Sudipta
Manna, Saikat Kumar
ARKIVOC, 2019, : 256 - 292
[4] Anticancer 5-arylidene-2-(4-hydroxyphenyl)aminothiazol-4(5H)-ones as tubulin inhibitors
Rehulka, Jiri
Subtelna, Ivanna
Kryshchyshyn-Dylevych, Anna
Cherniienko, Alina
Ivanova, Aleksandra
Matveieva, Mariia
Polishchuk, Pavel
Gurska, Sona
Hajduch, Marian
Zagrijtschuk, Oleh
Dzubak, Petr
Lesyk, Roman
ARCHIV DER PHARMAZIE, 2022, 355 (12)
[5] Regioselective one-pot synthesis of functionalised 6,7-dihydro-1H-indol-4(5H)-ones
Alizadeh, Abdolali
Bayat, Fahimeh
JOURNAL OF CHEMICAL RESEARCH, 2015, (03) : 166 - 169
[6] Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide
Jebali, Khaoula
Arfaoui, Aicha
Saadi, Fatma
Lebreton, Jacques
Amri, Hassen
SYNTHETIC COMMUNICATIONS, 2014, 44 (23) : 3400 - 3407
[7] Synthesis, Characterization and Cytotoxicity Evaluation of New Compounds from Oxazol-5(4H)-Ones and 1,2,4-Triazin-6(5H)-Ones Classes
Rosca, Elena Valentina
Apostol, Theodora Venera
Draghici, Constantin
Olaru, Octavian Tudorel
Socea, Laura Ileana
Iscrulescu, Lucian
Saramet, Gabriel
Barbuceanu, Florica
Pahontu, Elena Mihaela
Baraitareanu, Stelian
Barbuceanu, Stefania Felicia
REVISTA DE CHIMIE, 2019, 70 (11): : 3769 - 3774
[8] Synthesis, structure and antimicrobial evaluation of new 3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl-thiazol-4(5H)-ones
Gautam, Deepika
Chaudhary, R. P.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2015, 135 : 219 - 226
[9] 3-(α-Chlorobenzyl)quinoxalin-2(1H)-ones as Versatile Reagents for the Synthesis of 3-Benzylquinoxalin-2(1H)-ones and Thiazolo[3,4-a]quinoxalin-4(5H)-ones
Mamedov, Vakhid A.
Zhukova, Nataliya A.
Syakaev, Victor V.
Beschastnova, Tat'yana N.
Kadyrova, Milyausha S.
Isaeva, Anastasiya O.
Mamedova, Sevil, V
Gavrilova, Elena L.
Latypov, Shamil K.
Sinyashin, Oleg G.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (08) : 2221 - 2234
[10] Photoinduced Annulation of N-Phenylbenzamides for the Synthesis of Phenanthridin-6(5H)-Ones
Wang, Nana
Wang, Ding
He, Yun
Xi, Jin
Wang, Tao
Liang, Yong
Zhang, Zunting
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (06) : 1150 - 1155

← 1 2 3 4 5 →