One-Pot Three-Component Condensations of 2,6-Diaminopyrimidin-4(3 H )-one, Aromatic Aldehydes, and Naphthols. Synthesis
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Pot Three-Component Condensations of 2,6-Diaminopyrimidin-4(3H)-one, Aromatic Aldehydes, and Naphthols. Synthesis of Isomeric Benzochromeno[2,3-d]pyrimidines A. A. Harutyunyana,b,*, S. G. Israyelyana, H. A. Panosyana, and T. R. Hovsepyana a
Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, 0014 Armenia b
Russian–Armenian University, Yerevan, 0051 Armenia *e-mail: [email protected]
Received February 19, 2020; revised April 17, 2020; accepted April 19, 2020
Abstract—One-pot three-component reactions of 2,6-diaminopyrimidin-4-(3H)-one with aromatic aldehydes and 1- or 2-naphthol afforded benzo[7,8]chromeno[2,3-d]pyrimidine and benzo[5,6]chromeno[2,3-d]pyrimidine derivatives, respectively. In both cases, the heterocyclization involved substitution of the 6-amino group of 2,6-diaminopyrimidin-4-(3H)-one by hydroxy group of naphthol and closure of 4H-pyran ring, whereas no alternative benzopyrimidoquinoline derivatives were formed. Keywords: 2,6-diaminopyrimidin-4-(3H)-one, 1- and 2-naphthols, aromatic tion, benzo[7,8]chromeno[2,3-d]pyrimidines, benzo[5,6]chromeno[2,3-d]pyrimidines
aldehydes,
condensa-
DOI: 10.1134/S1070428020070143 Fused polycyclic pyrimidine derivatives, in particular benzochromenopyrimidines, have been extensively studied as promising compounds for the preparation of drugs and materials for industrial applications. Benzochromenopyrimidines were found to exhibit antibacterial, fungicidal [1], and antitumor activities [2] and act as NPSR (neuropeptide S receptor) antagonists [3]. They also show chemo-optical properties, which makes them promising for the design of dyes and fluorescent visualizers for biomedical studies and laser technologies [4]. One-pot three-component condensation of 2,6-diaminopyrimidin-4-(3H)-one (1) with aromatic aldehydes 2 and naphthalen-1-ol (3) or naphthalen-2-ol (4) in acetic acid gave new derivatives of isomeric heterocyclic systems, benzo[7,8]chromeno[2,3-d]pyrimidines 5a–5f and benzo[5,6]chromeno[2,3-d]pyrimidines 6a– 6i (Schemes 1, 2). It should be noted that, with a few exceptions [5], sparse examples of the synthesis of substituted benzochromeno[2,3-d]pyrimidines do not allow direct introduction of an amino group into the 9-position of the tetracyclic system due to structural requirements imposed on the initial reactants, which determine heterocyclization pathways.
The reaction of 1 with 2 and naphthalen-2-ol (4) afforded exclusively angularly fused 9-amino-12-aryl10,12-dihydro-11H-benzo[5,6]chromeno[2,3-d]pyrimidin-11-ones 6, whereas no alternative linearly fused isomer 7 was detected. This is consistent with published data [6], according to which 2-naphthols react at the 1-position rather than at the 3-position. The described condensations involved substitution of the 6-amino group of initial pyrimidine 1 by hydroxy group of naphthol and closure of 4H-pyran ring, whereas alternative heterocyclization pathway leading to benzopyrimidoquinoline system was not operative. Presumably, t
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