Construction of Polyheterocyclic Compounds by Lewis Acid Mediated Intramolecular [3+2] Cycloaddition Reaction

被引:3
作者
Dahiya, Pooja [1 ]
Yadav, Anoop [1 ]
Budhwan, Rajnish [1 ]
Peddinti, Rama Krishna [1 ]
机构
[1] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, Uttarakhand, India
关键词
domino reactions; cycloadditions; heterocyclic compounds; pyrrole-fused scaffolds; synthetic methods; N BOND FORMATION; BIOLOGICAL EVALUATION; DOMINO REACTION; C-C; PYRROLE; CYCLIZATION; DERIVATIVES; FUNCTIONALIZATIONS; POLYMERIZATION; ANTICANCER;
D O I
10.1002/ejoc.202300251
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient domino approach has been developed for the synthesis of polyheterocyclic derivatives constituting pyrrole moiety. Lewis acid catalyzed reaction of 2-substituted-2-hydroxy-indane-1,3-diones and 1,4-benzoxazinone derivatives resulted in the formation of polyheterocyclic compounds under metal-free and mild conditions in good to excellent yield. The reaction is highly regioselective for C-C and C-N bond construction proceeded via intramolecular [3+2] cycloaddition reaction. The protocol is highly efficient, obviates column chromatography and the products are obtained by simple filtration followed by washing with solvent.
引用
收藏
页数:6
相关论文
共 50 条
[21]   The asymmetric construction of CF3-containing spiro-thiazolone-pyrrolidine compounds via [3+2] cycloaddition [J].
Li, Boyu ;
Liu, Jikun ;
Gao, Fengyun ;
Sun, Mengmeng ;
Guo, Yifei ;
Zhou, Yuan ;
Wen, Dongwa ;
Deng, Yabo ;
Chen, Hui ;
Wang, Kairong ;
Yan, Wenjin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (11) :2892-2895
[22]   Tandem [3+2] cycloaddition reaction of azo-alkenes and thiocyanic acid: Extending the scope of the classical "Criss-cross" cycloaddition reaction [J].
Schantl, JG ;
Nadenik, P .
SYNLETT, 1998, (07) :786-788
[23]   Base-Mediated Tandem [3+2] Cycloaddition/Ring Openning Reaction of Arylhydrazonoyl Chlorides with Arylnitroso Compounds for Synthesis of Substituted Diazene Oxides [J].
Li, Yi ;
Xu, Weinan ;
Lei, Xidan ;
Xi, Jiangbo ;
Zou, Jing ;
Wang, Gang ;
He, Zhao-Lin .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19) :14200-14204
[24]   Synthesis of functionalized pyrroles and fused pyrroles through intermolecular [3+2] cycloaddition reaction [J].
Prasad, Pulaganti Vijaya ;
Shanker, Medi ;
Venkanna, Avudoddi ;
Swamy, Marapala Kumara ;
Gopichand, K. ;
Rao, Pallapothula Venkateswar .
SYNTHETIC COMMUNICATIONS, 2018, 48 (09) :1040-1044
[25]   Cobalt Porphyrin Catalyzed [3+2] Cycloaddition of Cyclopropanes and Carbonyl Compounds [J].
Shiba, Takahiro ;
Kuroda, Daiki ;
Kurahashi, Takuya ;
Matsubara, Seijiro .
SYNLETT, 2014, 25 (14) :2005-2008
[26]   Synthesis ofnew-type1,3,6-triazocinevia intramolecular reactions of iodocyclization and [3+2] azido cycloaddition [J].
Vaskevych, Ruslan, I ;
Vaskevych, Alla, I ;
Rusanov, Eduard B. ;
Mel'nyk, Oksana Ya ;
Vovk, Mykhailo V. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (08) :3202-3212
[27]   Dehydrogenation/(3+2) Cycloaddition of Saturated Aza-Heterocycles via Merging Organic Photoredox and Lewis Acid Catalysis [J].
Xiao, Teng-Fei ;
Zhang, Yi-Fan ;
Hou, Wen-Tao ;
Yan, Pen-Ji ;
Hai, Jun ;
Xu, Peng-Fei ;
Xu, Guo-Qiang .
ORGANIC LETTERS, 2021, 23 (22) :8942-8946
[28]   A novel non-metathetic behavior of Grubbs catalyst: Ruthenium-mediated intramolecular [3+2] cycloaddition of bis-1,3-dienes [J].
Takagi, Ryukichi ;
Yamamoto, Koumei ;
Hiraga, Yoshikazu ;
Kojima, Satoshi ;
Abe, Manabu .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 723 :171-175
[29]   First diastereoselective [3+2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides [J].
Arroniz, Carlos ;
Molina, Juan ;
Abas, Sonia ;
Molins, Elies ;
Campanera, Josep M. ;
Javier Luque, F. ;
Escolano, Carmen .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (10) :1640-1649
[30]   Dearomative [3+2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides [J].
Wang, Kai-Kai ;
Xie, Yan-Xin ;
Li, Yan-Li ;
Chen, Rongxiang ;
Wang, Zhan-Yong .
RSC ADVANCES, 2020, 10 (48) :28720-28724