Naphtho pyrimidines

Pyrimidine (1) is the trivial name for 1,3-diazine two me/a-oriented CH units in benzene have been replaced by nitrogen atoms. Quinazoline (2) is benzo-fused pyrimidine and is defined by the fusion nomenclature as benzo[if]pyrimidine, alternatively as 1,3-diazanaphthalene by the replacement nomenclature. Perimidine (3) is the trivial name for the pen -naphtho-fused pyrimidine system. It may be called (fusion names) l//-benzo[f/e]quinazoline or l//-naphtho[l,8-r/e]pyrimidine, or alternatively l//-l,3-diazaphenalene by the replacement nomenclature. However, the three trivial names are all system names accepted by lUPAC and approved as parents for further fusion name formation the benzo- and naphtho-pyrimidine names are therefore not used. In principle, additional rings can be fused onto the benzo or naphtho moiety in either quinazoline or perimidine without any profound alteration in heterocyclic reactivity. Aceperimidylene (4) and aceperimidine (5) are the trivial names for two cyclopenteno and cyclopentano fused perimidines. 

Pyrimidine 1 is the lUPAC accepted name for 1,3-diazabenzene, while quinazoline 2 is the accepted name for benzo[r lpyrimidine or 1,3-diazanaphthalene. Perimidine 3 is the lUPAC accepted name for l//-benzo[r/ ]quinazoline or H -naphtho[l,8-r/i ]pyrimidine, while benzo. 4]perimidine 4 is also known as 1,3-diazapyrene. 

Benzoselenadiazoles were synthesized at room temperature in the solid state with ortho-aromatic diamines and selenium dioxide. Diamines and selenium dioxide were ground, respectively, and then were mixed in a ratio of 1 1 in a mortar at room temperature the process was monitored with X-ray diffraction (XRD) or IR. The results showed that the reactions were completed after 30 min of grinding and the desired products were obtained. The yields of the synthesized compounds are as follows 2,1,3-benzoselenadiazole 196 77% l,2,5-selenadiazolo-[3,4-A]pyridine 284 44% l,2,5-selenadiazolo[3,4-c]pyridine 285 23% 5-methyl-2,l,3-benzo-[3,4-c]selenadiazole 286 74% 1,2,5-selenadi-azole[3,4- /]pyrimidine-7-(6/7)-one 287 50% 5,7-dihydroxy-l,2,5-selenadiazolo-[3,4- 7]pyrimidine 288 19% and 2,l,3-naphtho-[2,3-c]-selenadiazole (289) 77% <2004MI1>. 

Finally, some miscellaneous fused systems containing thiophene rings have attracted some interest. The electrophilic chemistry of several thia-PHAs has been investigated, among others benzo[Z>]naphtho[2,l-c/]thiophene , whereas an approach to related partially saturated systems from tetrahydrothiophene-3-one has been published <07TL4715>. It should also be mentioned that a 4-armno-7-ar ithieno 3,2-<7 pyrimidine library has been prepared <07JCC431>. 

Isocyanat 2-Cyan-2-methyl-l-phenyl-ethenyl- E4, 798 (2-NH2-en-CN + COCl2) Isoquinolo 4,3-d -l,3-oxazol 2-Methyl- E8a, 1088 (4-N3-iso-quinolin + H3C —COOH) Malonaldehydsiinre (4-Cyanmethyi-phenyl)- -nitril E3, 15 Naphtho(2,3-d -l,2-oxazol 3-Amino-E8a, 242 [2-OH — naphth. — 3-C(NH2)=N — O — COOR/A] lH-< Naphtho 1,8a,8-d,e]pyrimidin) ... 

Oxazolo[5,4-d]pyrimidines, synthesis and reactivity of 86AKZ211. Perimidines (naphtho[l,8-general review 81 UK 1559. Pyrido[l,2-fl]pyrimidines, chemistry of 83AHC(33)241. 

Fisher, G.J. and Land, E.L. (1983) Photosensitization of pyrimidines by 2-methyl-naphtho-quinone in water a laser flash photolysis study, Photochem. Photobiol., 37 27-32. 

El-Baih in 2004, has described the synthesis of naphtho[l,2-d]thiazolo[3,2-ajpyrimidine 10 (Scheme 3), by reaction of 2-arylmethylidene-l-tetralone 8 with thiourea under basic conditions to give naphtho[l,2-d]pyrimidine 9 which then cyclized with chloroacetic acid to afford the target compound 10 [21]. 

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