Novel succinct routes to quinoxalines and 2-benzimidazolylquinoxalines via the Ugi reaction

被引：34

作者：

Ayaz, Muhammad

Xu, Zhigang

Hulme, Christopher ^{[1
]}

机构：

[1] Univ Arizona, Oro Valley BIO5, Coll Pharm, Oro Valley, AZ 85737 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 23期

关键词：

Ugi reaction; Post-condensation modifications; Quinoxaline; Benzimidazole; Acyl transfer; SOLUTION-PHASE PREPARATION; ONE-POT; DERIVATIVES; EFFICIENT; LIBRARIES; PROTOCOL; MILD;

D O I：

10.1016/j.tetlet.2014.04.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This Letter reveals a unique, user-friendly, concise two-step, one-pot protocol for the synthesis of highly substituted quinoxalines. Conducting the Ugi reaction with appropriately functionalized classical Ugi reagents with subsequent acid treatment of the Ugi adduct affords collections of diversified quinoxalines in good to excellent yields. The methodology exploits what may be viewed as a 'convertible carboxylic acid', which in addition may be captured in an intramolecular sense to generate structurally complex 2-benzimidazolylquinoxalines in a mere two steps. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3406 / 3409

页数：4

共 50 条

[21] Rh(III)-Catalyzed C-2 Alkylation of Indoles followed by a Post-Synthetic Modification via the Ugi Reaction
Januario, Marcelo Augusto Pereira
de Souza, Demetrius P.
Zukerman-Schpector, Julio
Correa, Arlene G.
CHEMISTRYOPEN, 2023, 12 (06)
[22] Synthesis of novel glutarimide derivatives via the Ugi multicomponent reaction: affinity towards the E3 ubiquitin ligase substrate receptor Cereblon
Barkhatova, Darina
Zhukovsky, Daniil
Heim, Christopher
Maiwald, Samuel
Hartmann, Marcus D.
Krasavin, Mikhail
MENDELEEV COMMUNICATIONS, 2022, 32 (06) : 747 - 749
[23] Facile synthesis of functionalized 1H-pyrrolo[2,3-b]quinolines via Ugi four-component reaction followed by Cu-catalyzed aryl-amide, C-N bond coupling
Asthana, Mrityunjaya
Kumar, Ritush
Gupta, Tanu
Singh, Radhey M.
TETRAHEDRON LETTERS, 2015, 56 (07) : 907 - 912
[24] Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction
Keivanloo, Ali
Fakharian, Mahsa
Nabid, Mohammad Reza
Amin, Amir Hossein
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (01) : 151 - 160
[25] The Synthesis of Novel 7-(Substituted benzyl)-4,5-dihydro[1,2,3]triazolo[1,5-a]pyrazin-6(7H)-ones via Tandem Ugi-Huisgen Reactions
Pokhodylo, Nazariy T.
Tupychak, Mykola A.
Goreshnik, Evgeny A.
Obushak, Mykola D.
SYNTHESIS-STUTTGART, 2022, 55 (06): : 977 - 988
[26] Synthesis of novel 2,2-disubstituted naphthodioxoles via an unprecedented reaction
Kumar, Satish
Pallvi
Chadha, Shally
Dham, Sumita
Hundal, Tanya
Kapoor, Kamal K.
TETRAHEDRON LETTERS, 2012, 53 (15) : 1905 - 1907
[27] Novel 1,2,3,4-Tetrahydroquinazolinones via Reaction of 2-Amino-N-substituted Benzamides and Dimethyl Acetylenedicarboxylate
Nahavandian, Semiramis
Allameh, Sadegh
Saeedi, Mina
Ansari, Shirin
Mahdavi, Mohammad
Foroumadi, Alireza
Shafiee, Abbas
HELVETICA CHIMICA ACTA, 2015, 98 (07) : 1028 - 1033
[28] Synthesis of 2-Tetrazolyl-Substituted 3-Acylpyrroles via a Sequential Ugi-Azide/Ag-Catalyzed Oxidative Cycloisomerization Reaction
Kong, Han-Han
Pan, Hong-Ling
Ding, Ming-Wu
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) : 12921 - 12930
[29] Orthogonal sp3 C1-H and N-H Bond Functionalization of 1,2,3,4-Tetrahydroisoquinolines via the Ugi Four-Component Reaction
Yan, Ji-Min
Bai, Qi-Fan
Xu, Chang
Feng, Gaofeng
SYNTHESIS-STUTTGART, 2016, 48 (21): : 3730 - 3742
[30] Synthesis of novel oxindolylpyrrolo[2,3-d]pyrimidines via a three-component sequential tandem reaction
Rad-Moghadam, Kurosh
Azimi, Seyyedeh Cobra
TETRAHEDRON, 2012, 68 (47) : 9706 - 9712

← 1 2 3 4 5 →