- On the behaviour of 4- or 7-chloro-2-nitroindazole against cyclic amines. Part 35: Azoles
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The nitration of 4- or 7-chloroindazole (1, 9) to 4- or 7-chloro-2-nitroindazole (2, 11) is described. 4- or 7-chloro-3-nitroindazole (3, 12) and 4-chloro-1-nitroindazole (4) have been isolated as by-products. On treating with morpholine, pyrrolidine, piperidine and N-methylpiperazine 2 and 11 are transformed to the corresponding 3-amino-4- or 7-chloroindazoles 5-8,13-16 and 4- or 7-chloro-3-nitroindazole (3, 12). The isomerization of 2 to 3 takes also place under the influence of temperature.
- Majewska,Wrzeciono
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p. 688 - 691
(2007/10/02)
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- Aromatic Diazonium Salts, X. - A One-Pot Procedure for the Jacobson Synthesis of Indazole
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Procedures are described for a one-pot synthesis of 1H-indazole and substituted indazoles 3 in good yield (Table 1) from o-toluidines 2, alkyl nitrite or nitrous oxides, potassium acetate, and acetic anhydride in benzene.The spectroscopic properties of substituted indazoles (Tables 2-4) are discussed. - 4-Phenylcinnoline (18) is prepared by the same procedure from o-(α-methylenebenzyl)aniline.
- Ruechardt, Christoph,Hassmann, Volker
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p. 908 - 927
(2007/10/02)
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