A Straightforward Approach to Substituted 2-(Hydroxymethyl)-2,3-dihydrofuro[2,3-b] pyridines and 3-Hydroxy-3,4-dihydro-2H-pyrano[ 2,3-b] pyridines

被引：6

作者：

Hajbi, Youssef ^{[1
,2
]}

Suzenet, Franck ^{[1
]}

Khouili, Mostafa ^{[2
]}

Lazar, Said ^{[3
]}

Guillaumet, Gerald ^{[1
]}

机构：

[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, UMR 6005, F-45067 Orleans, France

[2] Univ Sultan Moulay Slimane, Lab Chim Organ & Analyt, Beni Mellal 23000, Morocco

[3] Univ Hassan II Mohammedia Casablanca, Lab Biochim Environm & Agroalimentaire, URAC 36, Mohammadia 20800, Morocco

来源：

SYNTHESIS-STUTTGART | 2010年 / 08期

关键词：

alkynes; cycloadditions; Diels-Alder reactions; fused-ring systems; heterocycles; DIELS-ALDER REACTIONS; INVERSE INTRAMOLECULAR <4&2>CYCLOADDITIONS; POTENTIAL ANXIOLYTIC AGENTS; 5-HT1A RECEPTOR LIGANDS; 1,2,4-TRIAZINES; 2,3-CYCLOPENTENOPYRIDINES; 1,2,4,5-TETRAZINES; 1,3,5-TRIAZINES; 2-AMINOPYRROLES; DERIVATIVES;

D O I：

10.1055/s-0029-1218665

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to 2-(hydroxymethyl)-2,3-dihydrofuro[ 2,3-b]pyridines and 3-hydroxy-3,4-dihydro-2H-pyrano[2,3b]pyridines is reported. The strategy is based on an intramolecular inverse electron demand Diels-Alder reaction starting from 1,2,4-triazines. The hydroxy function comes from the glycidol ring opening with alkynyllithium or alkynylorganoalane.

引用

页码：1349 / 1355

页数：7

共 50 条

[31] Synthesis of Functionalized H-[1]Benzopyrano[2,3-b]pyridines by the Friedlander Approach: Antimycobacterial and Antimicrobial Profile [J].

Haveliwala, Dhaval D. ;

Kamdar, Nimesh R. ;

Mistry, Prashant T. ;

Patel, Saurabh K. .

HELVETICA CHIMICA ACTA, 2013, 96 (05) :897-905

[32] An efficient approach for the synthesis of 5-hydroxy-chromeno[2,3-b]pyridines under catalyst and solvent free conditions [J].

Gupta, Shruti ;

Khurana, Jitender M. .

GREEN CHEMISTRY, 2017, 19 (17) :4153-4156

[33] Thieno[2,3-b]pyridines-A new class of multidrug resistance (MDR) modulators [J].

Krauze, Aivars ;

Grinberga, Signe ;

Krasnova, Laura ;

Adlere, Ilze ;

Sokolova, Elina ;

Domracheva, Ilona ;

Shestakova, Irina ;

Andzans, Zigmars ;

Duburs, Gunars .

BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (21) :5860-5870

[34] Unravelling the anticancer potential of functionalized chromeno[2,3-b ] pyridines for breast cancer treatment [J].

Oliveira-Pinto, Sofia ;

Pontes, Olivia ;

Lopes, Diogo ;

Sampaio-Marques, Belem ;

Costa, Marta D. ;

Carvalho, Luisa ;

Goncalves, Celine S. ;

Costa, Bruno M. ;

Maciel, Patricia ;

Ludovico, Paula ;

Baltazar, Fatima ;

Proenca, Fernanda ;

Costa, Marta .

BIOORGANIC CHEMISTRY, 2020, 100

[35] ONE-POT SYNTHESIS OF 2,3-DIARYLTHIENO[2,3-b]-, -[2,3-c]- OR -[3,2-c]PYRIDINES FROM THE RESPECTIVE ARYL(CHLOROPYRIDINYL)METHANONES [J].

Kobayashi, Kazuhiro ;

Ohmichi, Taira ;

Miyatani, Wataru ;

Nakagawa, Kazuhiro ;

Yuba, Shohei .

HETEROCYCLES, 2013, 87 (08) :1741-1748

[36] SYNTHESIS OF FURO[2,3-b]PYRIDINE [J].

Chang, Meng-Yang ;

Tai, Hang-Yi .

HETEROCYCLES, 2011, 83 (10) :2373-2380

[37] Photosensitized Intramolecular [2+2] Cycloaddition of 1H-Pyrrolo[2,3-b]pyridines Enabled by the Assistance of Lewis Acids [J].

Arai, Noriyoshi ;

Ohkuma, Takeshi .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) :15717-15725

[38] Synthesis of thieno[2,3-b]indoles (microreview) [J].

Egorov, Dmitry I. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (10) :779-781

[39] Novel pyrrolo[2,3-d]pyrimidines and pyrrolo[2,3-b]pyridines: design, synthesis, and in vivo TNF-α inhibitory activity [J].

Hilmy, Khaled M. H. ;

Abdul-Wahab, Hanan G. ;

Soliman, Dalia H. ;

Khalifa, Maha M. A. ;

Hegab, Amany M. .

MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (05) :2097-2110

[40] Pyridine-2(1H)-thiones: Versatile Precursors for Novel Pyrazolo[3,4-b]pyridine, Thieno[2,3-b]pyridines, and Their Fused Azines [J].

Sanad, Sherif M. H. ;

Abdel-Fattah, Azza M. ;

Attaby, Fawzy A. ;

Elneairy, Mohamed A. A. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (02) :651-662

← 1 2 3 4 5 →