Perimidines, 2,3-dihydro

S)-(-)-Perillyl alcohol. See Perillyl alcohol Perillyl aldehyde. See Perillaldehyde 1 H-Perimidine, 2,3-dihydro-2,2-dimethyl-6-((4-(phenylazo)-l-naphthyl) azo). See Solvent black 3 Periodic acid CAS 10450-60-9 Empirical HsIOe... 

H-Perimidine, 2,3-dihydro-2,2-dimethyl-6-((4-(phenylazo)-l-naphthyl) azo) 1H-Pyrimidine,... 

Other Names IH-Perimidine, 2,3-dihydro-2,2-dimeth-yl-6-[[4-(phenylazo)-l-naphthalenyl]azo]- C.I. Solvent Black 3 Sudan Black B 2,3-Dihydro-2,2-dimethyl-6-[(4-phenylazo-l-naphthalenyl)-azo]-l//-perimidine 2,3-Dihydro-2,2-dimethyl-6-[[4-(phenylazo)-l-naphthyl] azojperimidine 6-(l-Phenylazo-4-naphthylazo)-2,3-dihy-dro-2,2-dimethylperimidine Acetylated Sudan Black B Aizen SOT Black 6 C.I. 26150 Ceres Black BN Chuo Sudan Black 141 Fast Black HBN Fat Black HB Fat Black HB 01 Hexatype Black B Lacquer Black S Lacquer Black VB NSC 11239 Neptune Black X 60 Nubian Black BT Oil Black 860 Oil Black BT Oil Black HBB Oil Black HZ Orient Oil Black 860 Orient Oil Black HBB SOT-Black 6 Solvent Black 3 Sudan Black 141 Sudan Black X 60 Sudan Deep Black BB Sudan Deep Black BN Typogen Black... 

Similarly, the isolated salt 39 reacts with naphthalene-1,8-diamine in dichloromethane at room temperature to afford the 2,3-dihydro-l//-perimidine 78 in 85% yield (92SC3141) (Scheme 24). 

Valence and prototropic tautomeric reactions are among the most important mechanisms that govern transformations of a broad variety of photochromic organic systems.1,2 Until recently, no examples of photochromic compounds have been reported whose photochromic behavior was due to a combination of these two tautomeric reactions. Such a combination, which is characteristic of ring-chain tautomerism3 has been implemented in the photochromic and thermochromic rearrangements of a novel type of heterocyclic photochromes, derivatives of 2,3-dihydro-2-spiro-4 -(2, 6 -di-iert-butylcyclohexadien-2, 5 -one)perimidine la and its analogs.4 The occurrence of a proton transfer step is in accord with the fact that the AvV -dimethyl derivative of la exhibits no photochromic properties. 

On prolonged passing of air through ethanol or acetonitrile solutions of 1 (R = H) in a quartz photoreactor with an immersed mercury lamp, 2, 3 -dihydro-2 -spiro-4-(2,6-di- ert-butylcyclohexadien-2,5-one)perimidin-4 -one 14 was isolated as the main product of the photooxidation reaction. With the A W -dimethyl derivative of 1, photooxidation results in the formation of the perimidinedione 15.12... 

A mixture of 1,8-naphthalenediamine (3.48 g, 22 mmol), 2-tert-butyl-1,4-naphthoquinone (3.21 g, 15 mmol) and p-toluenesulfonic acid (50 mg) was melted together at 165-170°C for 4 h, cooled to room temperature and dissolved in chloroform (20 ml). The solution was passed through a column (40 x 3.5 cm) filled with A120 3. The column was washed with chloroform-hexane (1 3) and the fraction of orange color collected. After evaporation of the solvent, dark-yellow crystals of 2,3-dihydro-2-spiro-4 -[(4H)-2 -fert-butlnaphthalen-l -one]perimidine (2.06 g, yield 47.8%) were obtained, mp 211-213°C (after recrystallization from methanol and heptane). 

Dihydro 2,2-difnethylpeTimidiTte [called 2.2-Dlmethyl-2.3-dihydro-perimidin orN.N-Isopropyliden-naphthylendiamin-(1.8) in Ger],... 

Dihydro-2,2-dimethyl-4,6,7,9-tetronitro-perimidine or 4,6,7,9-Tetranitro-dimethyl-... 

Substituted benzo[i/,e]quinazolines (475, the perimidine ring system) are unaffected by NBH but are readily reduced to the 2,3-dihydro derivatives with LAH, yielding the 2,3-dihydroperimidines 476. The perimidones and thiones 477 are readily reduced to 478 on treatment with The... 

Carbon disulfide and 1,8-naphthalencdiamine react to give 2,3-dihydro-lH-perimidine-2-thione (XXXII) (297). 

Clearly, the success of an amination depends not only on the addition step but also on the ease of detachment of the hydride ion. According to the positive charge on the a-carbon atom in 1-methylperimidine (Table I), the compound should aminate faster than 1-methylbenzimidazole. The reason that it does not is attributed to the probability that the known fact that 2,3-dihydro-perimidine is extremely hard to aromatize (74CHE485 78CHE1156). 

Simple perimidines hardly fluoresce on irradiation with UV light, but 2,3-dihydro derivatives are... 

Six-membered heterocyclic systems which have been synthesised by similar methods include l,6-methano[10]annulenopyridines (214) from (213), y-carblines (215), lavendamycin methyl ester,a range of functionalised 2,3-dihydropyrido[3 ,2 4,5]thieno[3,2-d]pyrimidines (216), and the quinazolino[3,4-a]perimidine derivatives (e.g. 218) from 1,2-dihydro-properimidine azide (217). The previously unreported 4-methylene-4H-3,l-benzozazine ring (219) has been prepared from o-azidoacetophenone and the zwitterionic heteropolycyclic uracils (220) have been synthesised by a three-component reaction of iminophosphorane, isocyanate, and substituted pyridine. ... 

Dihydro-lH-perimidines. A mixture of 1,8-diaminonaphthalene and 4-[bis-(2-chlorethyl) amino] benzaldehyde in abs. ethanol heated 20 min. on a steam... 

H-indeno[l,2-e][l,4]diazepin-6-ones, 2,3-dihydro- 26, 373 perimidines 27, 497 -, 2-isothionreido-... 

Finally, the Se NMR evidence of l-mesityl-l,3-dihydro-imidazole-2-selone was much more consistent with the selone 43a (5( Se) = 28ppm, Vsec = 231 Hz] than with the selenol tautomer 43b (Scheme 5.34) [83]. The free energy of activation of prototropic tautomerism of ethyl 2H-perimidine-2-carboxylate 44 (Scheme 5.35)... 

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