ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
[4,4′-Bipyridine]-3,3′-diamine (1) reacts with HNO2 in H2SO4 to form 2,7,9,10-tetraazaphenanthrene (2) and 9H-pyrrolo[2,3-c:5,4-c′]dipyridine (3) instead of expected bipyridinediol 4 or furodipyridine 5. On the other hand, diazotization of 1 in hydrohalogenic acids leads to novel 3-halogeno-2,7,9,10-tetraazaphenanthrenes 10 or 11 and this reaction represents a new type of regioselective nucleophilic substitution of hydrogen atom in heteroaromatic species. The proposed pathway of reactions was supported by an experiment with the hypothetic intermediate, i.e. 2,7,9,10-tetraazaphenanthrene-9-imine (8), which was obtained on independent route.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19873290409
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