Skeletal rearrangement of arylmethylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones in the synthesis of the corresponding imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8-diones

被引：16
作者：
Izmest'ev, Alexei N. [1 ]
Vasileva, Darya A. [1 ,2 ]
Melnikova, Elizaveta K. [3 ,4 ]
Kolotyrkina, Natalya G. [1 ]
Borisova, Irina A. [1 ]
Kravchenko, Angelina N. [1 ]
Gazieva, Galina A. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Moscow 125047, Russia
[3] AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
[4] Lomonosov Moscow State Univ, Moscow 119991, Russia
来源：
NEW JOURNAL OF CHEMISTRY | 2019年 / 43卷 / 02期
基金：
俄罗斯基础研究基金会;
关键词：
BIOLOGICAL-ACTIVITY; ANTICANCER ACTIVITY; DERIVATIVES; DESIGN; INHIBITORS; DISCOVERY;
D O I：
10.1039/c8nj05058a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Z)-1,3-Dialkyl-7-arylmethylidene-1,3a,4,9a-tetrahydroimidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8(3H,7H)-diones have been prepared via a chemo- and diastereoselective aldol condensation of 1,3-dialkyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7(1H,6H)-diones with aromatic aldehydes followed by the skeletal rearrangement of thiazolotriazine fragments. We succeeded in synthesizing hitherto unknown products of alkali-induced skeletal rearrangement of 3a,9a-diphenyl substituted imidazothiazolotriazines.
引用
收藏
页码：1038 / 1052
页数：15
相关论文
共 44 条
[21]   Discovery of low-molecular-weight ligands for the AF6 PDZ domain [J].
Joshi, Mangesh ;
Vargas, Carolyn ;
Boisguerin, Prisca ;
Diehl, Annette ;
Krause, Gerd ;
Schmieder, Peter ;
Moelling, Karin ;
Hagen, Volker ;
Schade, Markus ;
Oschkinat, Hartmut .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3790-3795
[22]   Target-oriented analysis of gaseous, liquid and solid chemical systems by mass spectrometry, nuclear magnetic resonance spectroscopy and electron microscopy [J].
Kachala, V. V. ;
Khemchyan, L. L. ;
Kashin, A. S. ;
Orlov, N. V. ;
Grachev, A. A. ;
Zalesskiy, S. S. ;
Ananikov, V. P. .
RUSSIAN CHEMICAL REVIEWS, 2013, 82 (07) :648-685
[23]   5-Ene-4-thiazolidinones - An efficient tool in medicinal chemistry [J].
Kaminskyy, Danylo ;
Kryshchyshyn, Anna ;
Lesyk, Roman .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 140 :542-594
[24]   A SEM study of nanosized metal films and metal nanoparticles obtained by magnetron sputtering [J].
Kashin, A. S. ;
Ananikov, V. P. .
RUSSIAN CHEMICAL BULLETIN, 2011, 60 (12) :2602-2607
[25]   A convenient synthesis of 2-arylidene-5H-thiazolo[2,3-b]quinazoline-3,5[2H]-diones and their benzoquinazoline derivatives [J].
Khodair, AI .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (06) :1153-1160
[26]   Structural colors in nature: The role of regularity and irregularity in the structure [J].
Kinoshita, S ;
Yoshioka, S .
CHEMPHYSCHEM, 2005, 6 (08) :1442-1459
[27]   Physics of structural colors [J].
Kinoshita, S. ;
Yoshioka, S. ;
Miyazaki, J. .
REPORTS ON PROGRESS IN PHYSICS, 2008, 71 (07)
[28]   Structure-guided discovery of thiazolidine-2,4-dione derivatives as a novel class of Leishmania major pteridine reductase 1 inhibitors [J].
Leite, Franco Henrique A. ;
Gomes da Silva Santiago, Priscila Brandao ;
Froes, Thamires Quadros ;
da Silva Filho, Joao ;
da Silva, Suellen Goncalves ;
Ximenes, Rafael M. ;
de Faria, Antonio Rodolfo ;
Brondani, Dalci Jose ;
de Albuquerque, Julianna F. C. ;
Castilho, Marcelo Santos .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 123 :639-648
[29]   Synthetic and medicinal perspective of thiazolidinones: A review [J].
Manjal, Sundeep Kaur ;
Kaur, Ramandeep ;
Bhatia, Rohit ;
Kumar, Kapil ;
Singh, Virender ;
Shankar, Ravi ;
Kaur, Rupinder ;
Rawal, Ravindra K. .
BIOORGANIC CHEMISTRY, 2017, 75 :406-423
[30]   Acetic anhydride-promoted one-pot condensation of 2,4-thiazolidinedione with bisulfite adducts of aldehydes [J].
Mohanty, Sandeep ;
Roy, Amrendra Kumar ;
Kumar, Vinay K. P. ;
Reddy, Sandeep G. ;
Karmakar, Arun Chandra .
TETRAHEDRON LETTERS, 2014, 55 (33) :4585-4589
12345