Pyrazine properties

Table 3 lists some of the basic physical properties of pyrazine, quinoxaline and phenazine (references are given in the main text). 

Table 3 Physical Properties of Pyrazine, Quinoxaline and Phenazine...

Ring substituents show enhanced reactivity towards nucleophilic substitution, relative to the unoxidized systems, with substituents a to the fV-oxide showing greater reactivity than those in the /3-position. In the case of quinoxalines and phenazines the degree of labilization of a given substituent is dependent on whether the intermediate addition complex is stabilized by mesomeric interactions and this is easily predicted from valence bond considerations. 2-Chloropyrazine 1-oxide is readily converted into 2-hydroxypyrazine 1-oxide (l-hydroxy-2(l//)-pyrazinone) (55) on treatment with dilute aqueous sodium hydroxide (63G339), whereas both 2,3-dichloropyrazine and 3-chloropyrazine 1-oxide are stable under these conditions. This reaction is of particular importance in the preparation of pyrazine-based hydroxamic acids which have antibiotic properties. 

The Creutz-Taube anion, [(NH3)5Ru- N(CH=CH)2N Ru(NH3)5] + displays more obvious redox properties, yielding both 4+ and 6- - species, and much interest has focused on the extent to which the pyrazine bridge facilitates electron transfer. A variety of spectroscopic studies supports the view that low-energy electron tunnelling across the bridge delocalizes the charge, making the 5- - ion symmetrical. Other complexes, such as the anion [(CN)5Ru (/z-CN)Ru (CN)5] , are asymmetric... 

We wish to thank Professor F. W. Bergstrom for the sample of pyrazine, Dr. W. E. Vaughan for that of tetrabromobutane, Dr. K. J. Palmer for his help with experimental work, Dr. Sidney Weinbaum for assistance in the preparation of the figures, and Dr. E. R. Buchman for discussion of the chemical properties of the substances. We are especially indebted to Professor L. O. 

The adverse properties of red beet preparations are without doubt, their high nitrate content, their unpleasant smell due to pyrazine derivatives and geosmin with a low odor threshold, and finally the risk of carry-over of earth-bound germs. - " Since nitrate has been associated with nitrite and nitrosamine formation, the latter exhibiting cancer-inducing properties, procedures have been developed to reduce the nitrate content of red beet preparations. This has been achieved by microbial denitrification. - ... 

Our understanding of the physicochemical properties of pyrazines has deepened. The internal rotation and IR spectrum of 2,5-pyrazinedicarboxamide were studied by quantum chemical calculations <05TC73>, and ab initio MO calculations at the MP2/6-31++G( ) level were used to explain the electronic and vibrational properties of complexes of pyrazine and HX linear acids <05JMS2822>. MM and MO calculations were used to investigate the conformational and electronic properties of odor-active pyrazines <05JMS169>, and NMR, IR, X-ray, and DFT methods were used to examine the structures of pyridol l,2-a pyrazinium bromide <05JMS7>. 

The quinoxaline 100, with self-contained donor-acceptor properties, has potential in optoelectronic <06JACS10992>. Electroactive dendrimeric bis-quatemary salts have been prepared by direct quatemisation of pyrazine using dendrimeric benzyl bromides <06TL4711>. 

An efficient one-pot synthesis of some novel azolo[l,5-a]pyrimidines, via enaminonitriles, has been described <00SC1985>. The utility of 3-aminocinnamonitrile in the synthesis of new pyrazolo[l,5-a]pyrimidines has been reported <00ZN(B)321>. The synthesis of novel arylaminopyrazolo[3,4-d]pyrimidin-4-ones has been described <99IJC(B)1075>. The synthesis and properties of a-Thiagra, a substituted 5-(2-thienyl)pyrazolo[4,3-d]pyrimidin-7-one bioisostere of Viagra, have been described <00H(53)2643>. Imidazo[4,5-b]pyrazines are obtained by the reaction of 4-amino- 5-imino-imidazole derivatives with acetophenone dimethylacetal . 

It has been known that alternating LB films consisting of two different amphiphiles have noncentrosymmetric structures, and therefore, are expected to provide piezoelectric, pyroelectric and nonlinear optical properties. Therefore, we prepared alternating LB films consisting of 5-(p-dodecyloxyphenyl)pyrazine-2-carboxylic acid (DOPC)... 

Second-order nonlinear optical properties of noncentrosymmetric LB films composed of pyrazine derivatives... 

A similar but simpler 4-imino-hexahydropyrrolo[l,2-tf]pyrazin-l(277)-one 311 was prepared starting from the product obtained by nucleophilic substitution of a primary amine to the bromoacetamide of the L-prolylnitrile 310 (Scheme 40). The cyclization occurred directly in basic medium by refluxing for 96 h in EtOAc. This compound showed a potent activity as an orally bioavailable dipeptidyl peptidase IV inhibitor with anti-hyperglycemic properties <2003JME2774>. 

---