205989-13-5

Upstream product

• 205989-12-4 luotonin A 
• 75-05-8 acetonitrile 
• 725254-20-6 2-(2-quinolinyl)-3-hydroquinazolin-4-one 
• 68-12-2 N,N-dimethyl-formamide 
• 792923-90-1 2-(3-[1,3]dioxolan-2-yl)-1H-quinazolin-4-one 
• 35740-83-1 2-bromo-3-bromomethylquinoline 
• 792923-91-2 2-(3-[1,3]dioxolan-2-yl-quinolin-2-yl)-2,3-dihydro-1H-quinazolin-4-one 
• 530-53-0 deoxyvasicinone 
• 72081-99-3 N-hydroxyquinoline-2-carboximidamide 
• 1436-43-7 quinoline-2-carbonitrile 
• 5470-96-2 quinoline 2-carbaldehyde 
• 118-48-9 isatoic anhydride 
• 552-89-6 2-nitro-benzaldehyde 
• 26956-07-0 formyl-2 quinoleine carboxylate d'ethyle-3 

Relevant academic research and scientific papers

Iodine-mediated electrochemical C(sp3)-H cyclization: the synthesis of quinazolinone-fused N-heterocycles

An efficient iodine-mediated electrochemical C(sp3)-H cyclization was developed under mild conditions. A variety of functionalized quinazolinone-fused N-heterocycles can be obtained with good to excellent yields by virtue of this method. The reaction features a broad substrate scope and scalability, and is metal-free and chemical oxidant-free.

A concise approach to substituted Quinazolin-4(3H)-one natural products catalyzed by Iron(III) Chloride

A novel and efficient method for the synthesis of various Quinazolin-4(3H)-one natural products was developed utilizing Iron(III) Chloride catalyzed reaction as a key step. Circumdatin H, Bouchardatine, 8-Norrutaecarpine and, Luotonin B and E are few natu

A catalyst-free rapid, practical and general synthesis of 2-substituted quinazolin-4(3H)-ones leading to luotonin B and E, bouchardatine and 8-norrutaecarpine

A remarkably rapid but microwave/ultrasound/catalyst-free method has been developed for the construction of a quinazolin-4(3H)-one ring using formamide as an efficient ammonia precursor and PEG-400 as an effective solvent. The methodology afforded various 2-substituted quinazolin-4(3H)-one derivatives in good yield via a three-component reaction of isatoic anhydride, aldehydes and formamide in air. This single methodology was extended successfully to the synthesis of several alkaloids e.g. leutonin B and E, bouchardatine and 8-norrutaecarpine.

TBAHS-catalyzed synthesis of 2-dihydroquinazolin-2-ylquinoline: An efficient and practical synthesis of naturally occurring alkaloids luotonin A, B, and e

A synthesis of 2-dihydroquinazolin-2-ylquinoline using a phase-transfer catalyst (TBAHS) in semi-aqueous phase, followed by Mitsunobu cyclization as key steps for an efficient and practical synthesis of naturally occurring alkaloids luotonin A, B, and E starting from o-nitrobenzaldehyde is reported. The new approach presents the advantage of a shorter route with high overall yield (57%, 45%, and 37%, respectively) and ease of operation.

A concise and convergent synthesis of luotonin B and E

A concise and highly convergent practical synthesis of topoisomerase 1 inhibitor luotonin B was developed in a one-pot process in excellent yields. The C and D rings of luotonin B was constructed by cascade cyclizations of 2-cyanoquinoline-3-aldehyde or 2

Regioselective quinazolinone-directed ortho lithiation of quinazolinoylquinoline: Practical synthesis of naturally occurring human DNA topoisomerase I poison luotonin A and luotonins B and E

A regioselective quinazolinone-directed ortho lithiation on an adjacent quinoline moiety has been used as a key step for a short, efficient, and practical synthesis of the human DNA topoisomerase I poison luotonin A and luotonins B and E. The quinazolinoylquinoline 5 on treatment with in situ-generated nonnucleophilic mesityllithium furnished the desired dilithiated intermediate 6, which on treatment with formaldehyde followed by Mitsunobu ring closure reaction gave luotonin A (1a) in very good yield. The reaction of dilithiated intermediate 6 with DMF directly furnished luotonin B (1b) in 81% yield. Luotonin B (1b) on methylation with p-TSA/methanol gave luotonin E (1c) in 82% yield.

Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine

The total synthesis of luotonin A was achieved in excellent yield by using a Pd-assisted biaryl coupling reaction of N-(bromoquinolinyl)methylquinazolinone with Cy3P and KOAc. The successive treatment of luotonin A with NBS and aq. AgNO3 gave luotonin B in good yield. Although the Pd-assisted coupling reaction of N-(2-bromoindolyl)ethylquinazolinone with Cy3P and KOAc yielded rutaecarpine in poor yield, N-acetate under the same reaction conditions yielded the desired rutaecarpine directly in excellent yield. Graphical Abstract.

A short and efficient general synthesis of luotonin A, B and E

Highly convergent synthesis of three luotonins (A, B, and E) has been achieved from readily available starting materials. The key step in the synthesis is formation of quinazolinone skeleton by the condensation of 3-(1,3-dioxolan-2-yl-quinoline-2-carbaldehyde and anthranilamide. Graphical Abstract

Novel quinazoline-quinoline alkaloids with cytotoxic and DNA topoisomerase II inhibitory activities

Two new synthetic analogues of luotonins A and F, 7-acetylaminoluotonin A (6) and 3-[3H(quinazolino-4-one)]quinoline (7) were synthesized. The new analogues, along with four natural quinazoline-quinoline alkaloids, luotonins A (1), B (2), E (3), F (4) and a synthetic deoxoluotonin F (5), showed cytotoxic activity (IC50 1.8-40.0 μg/mL) and DNA topoisomerase II inhibition at a concentration of 25 μM.

A convenient synthesis of luotonins A and B

Total synthesis of the cytotoxic alkaloid, luotonin A, was achieved using a Pd-assisted biaryl coupling reaction of N-(bromoquinolinyl)methylquinazolinone with Cy3P and KOAc in high yield. Successive treatment of luotonin A with NBS and aqAgNO3 gave luotonin B in good yield.