Synthesis of New Furo[2,3‐d]pyrimidines and Pyrimido[4′,5′:4,5]furo[2,3‐d]pyrimidines

The title compound, C32H28N6O4·2C2H5OH, consists of two 2-(propylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one units connected, via one of the pyrimidine N atoms, to a bridging benzene ring in the 1,4 positions. Two ethanol solvent molecules are also present. The main molecule lies on a center of symmetry located at the center of the benzene ring. The fused-ring system of the benzofuro[3,2-d]pyrimidine moiety is nearly planar (r.m.s. deviation = 0.016 Å) and forms a dihedral angle of 78.21 (7)° with the central benzene ring. The crystal structure features O—H⋯O and N—H⋯O interactions. The C atoms of the propylamino side chain in the main molecule and the ethyl group in the solvent molecule are disordered over two positions, with site-occupancy factors 0.34:0.66 and 0.42:0.58, respectively.

Section: Related Literaturementioning

confidence: 99%

3,3′-(1,4-Phenylene)bis[2-(propylamino)benzofuro[3,2-d]pyrimidin-4(3H)-one] ethanol disolvate

Gong

et al. 2012

“…For the preparation and biological activity of benzofuropyrimidine derivatives, see: Moneam et al (2004); Bodke et al (2003). Forstacking interactions, see: Hu et al (2005Hu et al ( , 2006Hu et al ( , 2007Hu et al ( , 2008; Janiak (2000).…”

Section: Related Literaturementioning

confidence: 99%

“…Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008). Derivatives of benzofuropyrimidines are of great importance because of their remarkable biological properties, such as the interesting analgesic, antihypertensive, antipyretic, antiviral, and anti-inflammatory activities (Moneam et al, 2004 andBodke et al, 2003). Some X-ray crystal structures of benzofuro[3,2-d]pyrimidinone derivatives have been reported (Hu et al, 2005(Hu et al, , 2006(Hu et al, , 2007(Hu et al, , 2008.…”

Section: Data Collectionmentioning

confidence: 99%

2-(2-Hydroxyethylamino)-3-phenyl-1-benzofuro[3,2-d]pyrimidin-4(3H)-one dichloromethane hemisolvate

Zhang

Liu²,

Chen³

2009

In the title compound, C18H15N3O3·0.5CH2Cl2, the fused ring benzofuro[2,3-d]pyrimidine system is essentially planar [maximum deviation 0.029 (1) Å]. The planes of the pyrimidinone and phenyl rings are nearly perpendicular [dihedral angle = 87.50 (14)°]. The packing of the molecules in the crystal structure is governed mainly by intermolecular O—H⋯O and N—H⋯O hydrogen-bonding interactions and intermolecular π–π interactions between benzofuro[3,2-d]pyrimidine units [the interplanar distances are ca 3.4 and 3.5 Å, and the distances between adjacent ring centroids are in the range 3.64 (1)–3.76 (1) Å]. The dichloromethane solvent molecule lies on a special position.

“…For related literature on the synthesis and biological activity, see Moneam et al (2004); Bodke & Sangapure (2003). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al (2005Hu et al ( , 2006Hu et al ( , 2007.…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 2-[1-(4-chlorophenyl)-2,5-dioxo-1,2,3,5-tetrahydroimidazo[1′,2′:1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate

Hu¹,

Zhu

Chen

2007

The asymmetric unit of the title compound, C22H16ClN3O5, consists of two crystallographically independent molecules. The fused rings of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar and the chlorophenyl rings are twisted with respect to the two pyrimidinone ring systems by 71.00 (2) and 62.59 (2)°. The C atoms of the ethyl side chain are disordered and were refined using a split model. In the crystal structure, the molecules are connected via weak intra- and intermolecular C—H⋯O interactions are present. The ethyl group in one molecule is disordered over two positions, with site occupancy factors 0.55 and 0.45; in the other molecule only the methyl group is disordered over two positions, with site occupancy factors 0.6 and 0.4.