Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10488-10493

  Liu, Ji Feng ^a   Kaselj, Mira ^a   Isome, Yuko ^a   Chapnick, Jennifer ^a   Zhang, Bailin ^a   Bi, Grace ^a   Yohannes, Daniel ^a   Yu, Libing ^a   Baldino, Carmen M ^a  

^a ARQULE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MICROWAVES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DOMINO REACTIONS; MICROWAVE IRRADIATION; PROTOCOL; STARTING MATERIALS;

NITROGEN COMPOUNDS;

6,7 DIHYDRO 7 BENZYLQUINAZOLINO[3,2 A][1,4]BENZODIAZEPINE 5,13 DIONE; ALKALOID; ASPERLICIN; ASPERLICIN E; BENZODIAZEPINE DERIVATIVE; BENZOMALVIN A; CHOLECYSTOKININ RECEPTOR BLOCKING AGENT; CIRCUMDATIN E; CIRCUMDATIN F; NATURAL PRODUCT; NEUROKININ 1 RECEPTOR ANTAGONIST; PYRAZINE DERIVATIVE; PYRAZINO[2,1 B]QUINAZOLINE 3,6 DIONE; QUINAZOLINE DERIVATIVE; SCLEROTIGENIN; SUBSTANCE P ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; ASPERGILLUS OCHRACEUS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DRUG ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROWAVE IRRADIATION; NONHUMAN; PENICILLIUM; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALKALOIDS; BENZODIAZEPINES; BENZODIAZEPINONES; METHODS; MICROWAVES; PYRIMIDINONES; QUINAZOLINES;

EID: 28744448325     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051876x     Document Type: Article

References (40)

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33. The reactions were monitored by LC-MS.
34. "Symmetric" quinazolinobenzodiazepine alkaloids here refer to alkaloids originating from two identical 2-aminobenzoic acids, while "nonsymmetric" quinazolinobenzodiazepine alkaloids here refer to alkaloids originating from the two different 2-aminobenzoic acids.
35. The domino process requires 2 equiv of anthranilic acids 7 and 1 equiv of N-Boc amino acids 9 in the reaction mixture.
36. Since we encountered enantiomeric erosion in the synthesis of quinazolinone alkaloids with the pyrazino[2,1-6]quinazoline-3,6-dione core (ref 12), we elected to perform the syntheses of the racemates of the quinazolinobenzodiazepine alkaloids in the work described herein.
37. Although the yields are relatively low, they are still comparable or better than that of reported multistep syntheses (refs 6-10). The low yields may be attributed to the inefficient formation of the fused seven-membered rings, which resulted in the decomposion of the intermediates and generation of side products.
38. The first total synthesis of 4 was accomplished in six steps from 9d, see ref 8.
39. The O-methylation product was also isolated in 12% yield in an alkylation step, see the Experimental Section.
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