Cinnoline properties

F. W. Schulze, H. J. Petrick, H. K. Cammenga, H. Z. Klinge. Thermodynamic Properties of the Structural Analogues Benzo[c]cinnoline, trans-Azobenzene and cis-Azobenzene. Z. Phys. Chem. 1977, 107, 1-19. 

Durr et al. have described some novel complex cinnoline derivatives which show photochromic properties. Albini et al. have provided some new evidence on the mechanism for the photoisomerization of heterocyclic N-oxides. Simple pyridine N-oxides are exceptional. Thus irradiation of pyridine N -oxide in aqueous base affords the ring-opened product (23). Aoyama et al. have described the unprecedented photocyclization of the amide (24) to the lactam (25). The first examples of C2a+2Tr] photoreactions of a three-membered ring and an azo-compound have been described by Hunig and Schmitt. Nicolaou et al. have prepared the first stable example of a 1,2-dithiethane the procedure involves (2i +2Tr) photodimerization of C=S groups. 

Schulze, F.-W., Petrik, H.-J., Camenga K. H., and Klinge, H. (1977). Thermodynamic properties of the structural analogues benzo[c]cinnoline, Trans-azobenzene, and Cis-azobenzene. Z. Phys. Chem. (Wiesbaden) NF, 107, 1-19. 

The fluorescence and phosphorescence of quinazoline, 6-chloro-4-phenyl-and 6-chloro-l-methyl-4-phenylquinazolin-2(lH)-one were recorded in ethanol containing 1% of concentrated sulfuric acid. The luminescence of these compounds on thin-layer chromatography (TLC) plates saturated with ethanol was reported. 4-Morpholino- and 4-piperidino-6-methoxy-2-phenyl-quinazoline also have luminescent properties, and the ultraviolet fluorescence in the crystals and in hexane or benzene solution was discussed. The time and wavelength resolved emission from quinazoline vapor at low pressures was studied with a pulsed frequency double-dye laser and were compared with those of quinoxaline and cinnoline. ... 

A. Benzo[c]cinnoline Physical Properties and Bond Structure.168... 

V. Physical and Chemical Properties of Substituted Benzo [c]cinnolines.182... 

Ch. 1 General Introduction to Cinnoline Derivatives. Preparation and Properties of Citmoline... 

Any new or revised physical data for cinnoline and its salts or complexes may be found under cinnoline in the Appendix (Table A. 1) at the end of this book. More notable studies on the physical properties of cinnoline or reduced cinnoline are indicated briefly here. 

These two tables are intended as reasonably comprehensive lists of simple cinnolines (Table A.l) and simple phthalazines (Table A.2) described before 2005. For each compound are recorded (1) melting and/or boiling point(s) (2) an indication of reported spectra or other physical properties (3) any reported salts or simple derivatives, especially when the parent compound was un- or ill-characterized (4) an indication of an any simple complexes reported and (5) direct references to the original literature from 1972 onward, preceded by page references (in parentheses) to any earlier data reported in Simpson s Hauptwerk (e.g., H 70) or in Singerman and Patel s Ergdnzungswerk (e.g., E 324). 

Schulze FW, Petrick HJ, Cammenga HK, Klinge H. 1977. Thermodynamic properties of the structural analogs benzo[c]cinnoline, trans azobenzene, and cis azobenzene. Z Phys Chem (Muenchen, Ger) 107(1) 1 19. 

Cinnolines are known to exhibit anticancer, fungicidal and bactericidal, and antiinflammatory activity as well as luminescent and optical properties. In 2012, Willis and co-workers reported a one-pot two-step route to cinno-lines. By using 2-(2-bromoalkenyl) aryl bromide and diethyl-l,2-hydrazine dicarbo)ylate as the starting materials and copper as the catalyst, the desired dihydrocinnoline derivatives can be produced in moderate to good yields, which can give cinnolines after deprotection (Scheme 3.58). 

THE PROPERTIES OF FUNCTIONAL GROUPS 2- and 4-pyridyl compounds ss, 332, o-Amino-2-tolazole does not give a cinnoline when diazotized s. 

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