Download PDF by Author Unknown: Advances in Heterocycling Chemistry. Vol. 44

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ISBN-10: 0080576311

ISBN-13: 9780080576312

ISBN-10: 0120206447

ISBN-13: 9780120206445

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Sec. B] ADVANCES IN THE CHICHIBABIN REACTION 45 The amination of 1H-pyrrolo [2,3-f] isoquinoline (143)with excess sodium amide afforded 6-amino- 1H-pyrrolo[2,3-j'] isoquinoline (144)(Scheme 53) (84CHE399). The yield in xylene was 55% and in DMA it was 90%. The formation of 144 in liquid ammonia was observed by chromatography. Of the benzoquinolines, phenanthridine (14)was readily aminated in xylene or DMA to give 6-aminophenanthridine (15)(78RCR1042). Some derivatives of phenanthridine were aminated in xylene with sodium amide by Keene and Tissington (65JCS3032).

4) (72JA682; 73JOC1947). 5), much higher temperatures, usually over IOO’C, are required. 77) (72MIl; 73IJC825; 78RCR1042). 7) gave better yields than aromatic hydrocarbons (71CHE1036; 72CHE1131). There may be some solubility of the alkali metal amide in DMA, which leads to a more homogeneous reaction mixture (73RCR37). There is much need of a better solvent for the Chichibabin reaction having a boiling point significantly higher than ammonia. H. TEMPERATURE EFFECT The role of temperature can be important, especially for aminations taking place in liquid ammonia, where the reaction is often temperature dependent.

From Ref. 64Cl(L)710. From Ref. 56HCA505. From Ref. 84EUP0098684A2. From Ref. 83USP4386209. ’ sure amination of 3-picoline because it obviously occurred during the pressure amination of 2-picoline affording m-phenylenediamine as the predominant product (Section IV,B). The effect of temperature and pressure on the amination of 3-picoline is shown in Fig. 1. This was probably due to thermolysis playing an important role. Other 3-substituted pyridines behaved the same way as 3-picoline under pressure.

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Advances in Heterocycling Chemistry. Vol. 44 by Author Unknown

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