Journal
TETRAHEDRON LETTERS
Volume 121, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2023.154484
Keywords
Tricyclic quinazolinones; Iodocyclization; Intramolecular C-N bond formation; Deoxyvasicinones; Geminal dichloro conversion
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Two deoxyvasicinone analogues were synthesized via different linear cyclization processes from 2-(4-oxopentyl)quinazolin-4(3H)-ones. The first analogue, 1-acetyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one, was obtained through direct cyclization with I2 in basic conditions. The second analogue, 1-acetylpyrrolo[2,1-b]quinazolin-9(3H)-one, was synthesized via a two-step procedure involving geminal dichlorination in acidic conditions followed by intramolecular C-N bond formation in the presence of para-toluenesulfonic acid.
Two deoxyvasicinone analogues were obtained from 2-(4-oxopentyl)quinazolin-4(3H)-ones via different process of linear cyclizations. The first was 1-acetyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one ana-logue derived from direct cyclization in the presence of I2 in basic condition. The other was 1-acetylpyr-rolo[2,1-b]quinazolin-9(3H)-one analogue obtained from two-step procedures beginning with geminal dichlorination in acidic condition, followed by intramolecular C-N bond formation in the presence of para-toluenesulfonic acid.CO 2023 Elsevier Ltd. All rights reserved.
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