Cascade of the acylation/intramolecular oxo-Diels-Alder reaction for the diastereoselective synthesis of thienyl substituted hexahydropyrano [3,4-c]pyrrole-1,6-diones

被引：2

作者：

Zaytsev, Vladimir P. ^{[1
]}

Surina, Nataliya S. ^{[1
]}

Pokazeev, Kuzma M. ^{[1
]}

Shelukho, Evgeniya R. ^{[1
]}

Yakovleva, Elizaveta D. ^{[1
]}

Nadirova, Maryana A. ^{[1
]}

Novikov, Roman A. ^{[2
]}

Khrustalev, Victor N. ^{[3
,4
]}

Zubkov, Fedor I. ^{[1
]}

机构：

[1] RUDN Univ, Peoples Friendship Univ Russia, Organ Chem Dept, 6 Miklukho Maklaya St, Moscow 117198, Russia

[2] Russian Acad Sci, VA Engelhardt Inst Mol Biol, 32 Vavilov St, Moscow 119991, Russia

[3] RUDN Univ, Peoples Friendship Univ Russia, Inorgan Chem Dept, 6 Miklukho Maklaya St, Moscow 117198, Russia

[4] RAS, Zelinsky Inst Organ Chem, 47 Leninsky Prospect, Moscow 119991, Russia

来源：

TETRAHEDRON LETTERS | 2023年 / 120卷

关键词：

Intramolecular Diels-Alder reaction; Allylamines; IMODA reaction; IMDAV reaction; Thiophene; Pyrano[3; 4-c]pyrrole; CYCLOADDITION REACTIONS; ANTAGONIST; STRATEGY;

D O I：

10.1016/j.tetlet.2023.154434

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient approach toward the synthesis of functionalized hexahydropyrano[3,4-c] pyrrole-1,6-diones from readily accessible 3-thienylsubstituted allylamines and maleic anhydride. This transformation begins with the N-acylation of the allylamines with the anhydride, followed by the intramolecular oxo-Diels-Alder reaction (IMODA), which is accompanied by the tautomerization step, and ends with the formation of saturated pyrano[3,4-c]pyrroles. (c) 2023 Elsevier Ltd. All rights reserved.

引用

页数：5

共 44 条

[1] A Tandem [3+2] Cycloaddition-Elimination Cascade Reaction to Generate Pyrrolo-[3,4-c]pyrrole-1,3-diones
Martinez-Ariza, Guillermo
Dietrich, Justin
De Moliner, Fabio
Hulme, Christopher
SYNLETT, 2013, 24 (14) : 1801 - 1804
[2] Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives
Yang, Shanxue
Yao, Lan
Fan, Zhenhua
Han, Jing
Chen, Jie
He, Weimin
Deng, Hongmei
Shao, Min
Zhang, Hui
Cao, Weiguo
JOURNAL OF FLUORINE CHEMISTRY, 2021, 243
[3] (3+2) Cycloaddition reactions in the synthesis of C(4)-N(5)-condensed tetrahydropyrrolo[3,4-c]pyrrole-1,3-diones (microreview)
Medvedeva, Svetlana M.
Shikhaliev, Khidmet S.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (09) : 687 - 689
[4] Solid-phase synthesis of pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-diones.
Dong, LC
Gowravaram, MR
Li, JH
Dilip, U
Yao, GM
Gallop, MA
Needels, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U113 - U113
[5] (3+2) Cycloaddition reactions in the synthesis of C(4)–N(5)-condensed tetrahydropyrrolo[3,4-c]pyrrole-1,3-diones (microreview)
Svetlana M. Medvedeva
Khidmet S. Shikhaliev
Chemistry of Heterocyclic Compounds, 2016, 52 : 687 - 689
[6] Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels-Alder reaction
Fang, Ren-Jie
Yan, Chen
Sun, Jing
Han, Ying
Yan, Chao-Guo
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2425 - 2432
[7] PREPARATIVE FLASH VACUUM THERMOLYSIS - SYNTHESIS OF FURO[3,4-C]PYRIDINE BY RETRO DIELS-ALDER REACTION
WIERSUM, UE
ELDRED, CD
VRIJHOF, P
VANDERPLAS, HC
TETRAHEDRON LETTERS, 1977, (20) : 1741 - 1742
[8] An intramolecular oxo Diels-Alder approach to 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters
Murray, WV
Mishra, PK
Turchi, IJ
Sawicka, D
Maden, A
Sun, S
TETRAHEDRON, 2003, 59 (45) : 8955 - 8961
[9] Studies on intramolecular Diels-Alder reactions of furo[3,4-c]pyridines in the synthesis of conformationally restricted analogues of nicotine and anabasine
Sarkar, TK
Basak, S
Slanina, Z
Chow, TJ
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11): : 4206 - 4214
[10] Iodine-catalysed synthesis of thiopyrano[3,4-c]quinoline derivatives via imino-Diels-Alder reaction
Wang, Wei
Yin, Ming-Yue
Zhang, Mei-Mei
Wang, Xiang-Shan
JOURNAL OF CHEMICAL RESEARCH, 2012, (06) : 318 - 321

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