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Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

ABSTRACT: We report a synthetic methodology for the construction of the fused heterocyclic compounds pyrido[2,1-b]quinazolin-9(1H)-ones and pyrrolo[2,1-b]quinazolin-9(1H)-ones through an AgOTf-catalyzed intramolecular alkyne hydroamination reaction. The methodology is applicable to a wide scope of substrates and produces a series of fused quinazolinone heterocycles in good to excellent yields.

SUBMITTER: Wang H

PROVIDER: S-EPMC4419559 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions.

Wang Hengshuai H Jiao Shengchao S Chen Kerong K Zhang Xu X Zhao Linxiang L Liu Dan D Zhou Yu Y Liu Hong H

Beilstein journal of organic chemistry 20150330

We report a synthetic methodology for the construction of the fused heterocyclic compounds pyrido[2,1-b]quinazolin-9(1H)-ones and pyrrolo[2,1-b]quinazolin-9(1H)-ones through an AgOTf-catalyzed intramolecular alkyne hydroamination reaction. The methodology is applicable to a wide scope of substrates and produces a series of fused quinazolinone heterocycles in good to excellent yields. ...[more]

PMID: 25977715

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Project description:In the crystal, mol-ecules of the title compound, C(11)H(10)N(2)S, are connected by C-H?N inter-actions around threefold axes. Furthermore, they form stacks along the c axis showing ?-? inter-actions between pyrimidine rings [centroid-centroid distance = 3.721?(1)?Å]. The central ring is essentially planar with an r.m.s. deviation of 0.007?Å. The five-membered ring adopts an envelope conformation with the flap atom deviating by 0.241?(4)?Å from the mean plane (r.m.s. deviation = 0.002?Å) through the other four ring atoms.

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