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Synthesis 2007(21): 3390-3398
DOI: 10.1055/s-2007-990818
DOI: 10.1055/s-2007-990818
PAPER
© Georg Thieme Verlag Stuttgart · New York
Microwave-Assisted, Solvent-Free Synthesis of Several Quinazoline Alkaloid Frameworks
Further Information
Received
4 June 2007
Publication Date:
10 October 2007 (online)
Publication History
Publication Date:
10 October 2007 (online)
Abstract
Microwave irradiation leads to a considerable improvement of the cyclocondensation between anthranilic acid and lactim ethers derived from piperazine-2,5-diones in terms of reaction times, yields, and stereocenter integrity. This reaction has been used to prepare some derivatives of the pyrazino[2,1-b]quinazoline-3,6-dione system present in many quinazoline alkaloids. It could also be applied to the synthesis of compounds containing the complete hexacyclic ring system of the anti-MDR natural product N-acetylardeemin, and other comprising the pentacyclic framework of circumdatin E. The microwave-assisted reaction was also much better than the thermal one when applied to a bis-lactim ether, leading to the corresponding pentacyclic pyrazino[2,1-b:5,4-b′]diquinazoline-8,16-dione in excellent yield.
Key words
microwave irradiation - lactim ether - alkaloids - antitumor agents - heterocycles
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