Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation
- PMID: 16018661
- DOI: 10.1021/ol0513084
Novel one-pot total syntheses of deoxyvasicinone, mackinazolinone, isaindigotone, and their derivatives promoted by microwave irradiation
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.
Similar articles
-
Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids.J Org Chem. 2005 Dec 9;70(25):10488-93. doi: 10.1021/jo051876x. J Org Chem. 2005. PMID: 16323862
-
Three-component one-pot total syntheses of glyantrypine, fumiquinazoline F, and fiscalin B promoted by microwave irradiation.J Org Chem. 2005 Aug 5;70(16):6339-45. doi: 10.1021/jo0508043. J Org Chem. 2005. PMID: 16050695
-
Radical reactions with 3H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin.Org Biomol Chem. 2007 Jan 7;5(1):103-13. doi: 10.1039/b614075k. Epub 2006 Nov 3. Org Biomol Chem. 2007. PMID: 17164913
-
Alkaloids from Mackinlaya species and synthetic mackinazolinone derivatives: An overview.Bioorg Med Chem. 2025 Jan 1;117:118018. doi: 10.1016/j.bmc.2024.118018. Epub 2024 Nov 23. Bioorg Med Chem. 2025. PMID: 39591875 Review.
-
Microwave-assisted synthesis of bioactive quinazolines and quinazolinones.Comb Chem High Throughput Screen. 2007 Dec;10(10):903-17. doi: 10.2174/138620707783220356. Comb Chem High Throughput Screen. 2007. PMID: 18288950 Review.
Cited by
-
Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.Synthesis (Stuttg). 2013 Oct 6;45(13):1430-1748. Synthesis (Stuttg). 2013. PMID: 24052668 Free PMC article.
-
Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library.Mol Divers. 2023 Aug;27(4):1767-1783. doi: 10.1007/s11030-022-10529-y. Epub 2022 Oct 5. Mol Divers. 2023. PMID: 36197552
-
Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.Beilstein J Org Chem. 2015 Mar 30;11:416-24. doi: 10.3762/bjoc.11.47. eCollection 2015. Beilstein J Org Chem. 2015. PMID: 25977715 Free PMC article.
-
Synthesis of Novel N-Heterocyclic Compounds Containing 1,2,3-Triazole Ring System via Domino, "Click" and RDA Reactions.Molecules. 2019 Feb 21;24(4):772. doi: 10.3390/molecules24040772. Molecules. 2019. PMID: 30795610 Free PMC article.
-
Stereochemistry of the methyl-idene-bridged quinazoline-iso-quinoline alkaloid 3-{[6,7-dimeth-oxy-1-(4-nitro-phen-yl)-1,2,3,4-tetra-hydro-isoquinolin-2-yl]methyl-idene}-1,2,3,9-tetra-hydro-pyrrolo-[2,1-b]quinazolin-9-one methanol monosolvate.Acta Crystallogr E Crystallogr Commun. 2020 May 22;76(Pt 6):914-919. doi: 10.1107/S2056989020006696. eCollection 2020 Jun 1. Acta Crystallogr E Crystallogr Commun. 2020. PMID: 32523763 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources