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Literature DB >> 16018661

Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation.

Ji-Feng Liu¹, Ping Ye, Kevin Sprague, Katie Sargent, Daniel Yohannes, Carmen M Baldino, Christopher J Wilson, Shi-Chung Ng.

Abstract

[reaction: see text]. Total syntheses of deoxyvasicinone (1), mackinazolinone (2), and 8-hydroxydeoxyvasicinone (3) via novel microwave-assisted domino reactions, as well as a novel three-component one-pot total synthesis of isaindigotone (5) promoted by microwave irradiation, are reported. The efficient reaction process enabled us to rapidly access related natural product derivatives and to identify a new class of cytotoxic agents.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 16018661 DOI： 10.1021/ol0513084

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

Review 1. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors: C Oliver Kappe; Doris Dallinger
Journal: Mol Divers Date: 2009-04-21 Impact factor: 2.943

2. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors: Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal: Synthesis (Stuttg) Date: 2013-10-06 Impact factor: 3.157

3. Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library.

Authors: Buer Song; Lifei Nie; Khurshed Bozorov; Rustamkhon Kuryazov; Jiangyu Zhao; Haji Akber Aisa
Journal: Mol Divers Date: 2022-10-05 Impact factor: 3.364

4. Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

Authors: Hengshuai Wang; Shengchao Jiao; Kerong Chen; Xu Zhang; Linxiang Zhao; Dan Liu; Yu Zhou; Hong Liu
Journal: Beilstein J Org Chem Date: 2015-03-30 Impact factor: 2.883

5. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities.

Authors: Ghadamali Khodarahmi; Elham Jafari; Gholamhossein Hakimelahi; Daryoush Abedi; Marzieh Rahmani Khajouei; Farshid Hassanzadeh
Journal: Iran J Pharm Res Date: 2012 Impact factor: 1.696

Review 6. Microwave multicomponent synthesis.

Authors: Helmut M Hügel
Journal: Molecules Date: 2009-12-01 Impact factor: 4.411

Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation.

Review 1. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

2. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

3. Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library.

4. Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

5. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities.

Review 6. Microwave multicomponent synthesis.

7. Electro-oxidative cyclization: access to quinazolinones via K₂S₂O₈ without transition metal catalyst and base.

8. Synthesis and cytotoxic evaluation of some new 4(3H)-quinazolinones on HeLa cell line.

Review 9. Progress in the studies on rutaecarpine.

Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation.

Review 1. Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

2. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

3. Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library.

4. Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

5. Synthesis of some new quinazolinone derivatives and evaluation of their antimicrobial activities.

Review 6. Microwave multicomponent synthesis.

7. Electro-oxidative cyclization: access to quinazolinones via K2S2O8 without transition metal catalyst and base.

8. Synthesis and cytotoxic evaluation of some new 4(3H)-quinazolinones on HeLa cell line.

Review 9. Progress in the studies on rutaecarpine.

7. Electro-oxidative cyclization: access to quinazolinones via K₂S₂O₈ without transition metal catalyst and base.