The Reactions of p-Tosylmethyl Isocyanide with Aldehydes in the Synthesis of Heterocyclic Compounds: A Review

被引:0
作者
Vchislo, Nadezhda V. [1 ]
Fedoseeva, Victoria G. [1 ]
Verochkina, Ekaterina A. [1 ]
机构
[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, 1 Favorsky St, Irkutsk 664033, Russia
关键词
Aldehydes; p-tosylmethyl isocyanide; heterocycles; cycloaddition; catalysis; natural products; ONE-POT SYNTHESIS; 3,4-DISUBSTITUTED PYRROLES; MULTICOMPONENT REACTIONS; POLYSUBSTITUTED FURANS; PHOTOCHEMICAL APPROACH; CATALYZED SYNTHESIS; NATURAL-PRODUCTS; FACILE SYNTHESIS; SMALL-MOLECULE; IN-SILICO;
D O I
10.2174/1570193X19999220523113243
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
p-Tosylmethyl isocyanide (TosMIC) and its derivatives represent an important class of polyfunctional reagents, making them privileged "building blocks" in the targeted organic synthesis to design a plethora of heterocycles as well as natural products. This review summarizes and highlights the synthetic potential of p-tosylmethyl isocyanide and its derivatives in the reaction with various aldehydes to afford valuable heterocycles. The catalytic and technological innovations discussed in the review reveal the ease of reaction. Moreover, their mechanistic schemes are also displayed.
引用
收藏
页码:372 / 393
页数:22
相关论文
共 156 条
[21]   Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met [J].
Damghani, Tahereh ;
Moosavi, Fatemeh ;
Khoshneviszadeh, Mehdi ;
Mortazavi, Motahareh ;
Pirhadi, Somayeh ;
Kayani, Zahra ;
Saso, Luciano ;
Edraki, Najmeh ;
Firuzi, Omidreza .
SCIENTIFIC REPORTS, 2021, 11 (01)
[22]   Straightforward Assembly of Phenylimidazoquinoxalines via a One-Pot Two-Step MCR Process [J].
De Moliner, Fabio ;
Hulme, Christopher .
ORGANIC LETTERS, 2012, 14 (05) :1354-1357
[23]   In(OTf)3 catalysed an expeditious synthesis of β-carboline-imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazine conjugates [J].
Devi, Nisha ;
Singh, Dharmender ;
Honey ;
Mor, Satbir ;
Chaudhary, Sandeep ;
Rawal, Ravindra K. ;
Kumar, Vipin ;
Chowdhury, Asim K. ;
Singh, Virender .
RSC ADVANCES, 2016, 6 (50) :43881-43891
[24]   Functionalized Quinoxaline for Chromogenic and Fluorogenic Anion Sensing [J].
Dey, Sandeep Kumar ;
Al Kobaisi, Mohammad ;
Bhosale, Sheshanath V. .
CHEMISTRYOPEN, 2018, 7 (12) :934-952
[25]   Recent Progress in Iodine-Catalysed C-O/C-N Bond Formation of 1,3-Oxazoles: A Comprehensive Review [J].
Dhawan, Sanjeev ;
Kumar, Vishal ;
Girase, Pankaj S. ;
Mokoena, Sithabile ;
Karpoormath, Rajshekhar .
CHEMISTRYSELECT, 2021, 6 (04) :754-787
[26]   Ionic liquid (molten salt) phase organometallic catalysis [J].
Dupont, J ;
de Souza, RF ;
Suarez, PAZ .
CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691
[27]   Recent Advances in the Chemistry of Isocyanides with Activated Methylene Group [J].
Efimov, Ilya V. ;
Kulikova, Larisa N. ;
Zhilyaev, Dmitry I. ;
Voskressensky, Leonid G. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (47) :7284-7303
[28]   Synthesis of oxazolines and oxazoles by the reaction of propynals with tosylmethyl isocyanide [J].
Elshina, Victoria G. ;
Novokshonov, Vladimir V. ;
Verochkina, Ekaterina A. ;
Ushakov, Igor A. ;
Rosentsveig, Igor B. ;
Vchislo, Nadezhda V. .
MENDELEEV COMMUNICATIONS, 2019, 29 (06) :651-652
[29]   In silico-driven multicomponent synthesis of 4,5-and 1,5-disubstituted imidazoles as indoleamine 2,3-dioxygenase inhibitors [J].
Fallarini, S. ;
Massarotti, A. ;
Gesu, A. ;
Giovarruscio, S. ;
Zabetta, G. Coda ;
Bergo, R. ;
Giannelli, B. ;
Brunco, A. ;
Lombardi, G. ;
Sorba, G. ;
Pirali, T. .
MEDCHEMCOMM, 2016, 7 (03) :409-419
[30]   Copper-mediated direct sulfonylation of C(sp2)-H bonds employing TosMIC as a sulfonyl source [J].
Fan, Cai-Ling ;
Zhang, Lin-Bao ;
Liu, Jia ;
Hao, Xin-Qi ;
Niu, Jun-Long ;
Song, Mao-Ping .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) :2215-2219