Heterocyclic analogs of pleiadiene. XV. Direct acylation of perimidines in the naphthalene ring. Synthesis of 4 (9)- and 6 (7)-acylperimidines

It is shown that perimidines and aceperimidines are acylated by carboxylic acid or their anhydrides in polyphosphoric acid to give 6(7)-acylperimidines at 70–80° (kinetic control) and 4(9)-acylperimidines at 120–150° (thermodynamic control). Acetylation of the perimidines with acetic anhydride also takes place in the presence of perchloric acid.     

Investigations in the region of 2,3′-biquinolyl 4. Alkylation of the dianion of 2,3′-biquinolyl

With alkyl chlorides and alkyl phenyl ethers the dianion of 2,3-biquinolyl forms the products from alkylation at position 4. Their treatment with alkyl halides or water gives 1, 4-dialkyl-1, 4-dihydro-2,3-biquinolyls or 4-alkyl-1,4-dihydro-2,3-biquinolyls respectively.For communication 3, see [1].Stavropol State University, Stavropol, Russia 355009. Russian Chemical Technology University, Moscow 125190. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1214–1217, September, 1998.     

Heterocyclic analogs of pleiadiene. 70. Synthesis of 6-hydroxy-1,3-diazapyrenes

The regioselectivity of the reactions of perimidine with cinnamic acids in polyphosphoric acid (PPA) depends on the P₂O₅ content. Procedures were developed for the synthesis of 4(9)- and 6(7)-cinnamoylperimidines. Cyclization of the latter under the action of an excess of AlBr₃ was accompanied by dearylation to form 6-hydroxy-1,3-diazapyrene.     

Studies in the area of 2,3′-biquinolyl. 1. Arylation and hetarylation of 2,3′-biquinolyl dianion

The 2,3-biquinolyl dianion, when reacting with aryl- and hetaryl halides, forms arylation products at the 4 position, and treatment of these products with alkyl halides or water yields 1-alkyl-4-aryl-1,4-dihydro-2,3-biquinolyls or 4-aryl-1,4-dihydro-2,3-biquinolyls, respectively. Oxidation of the latter yields 4-aryl-2,3-biquinolyls. The cation dependence of the arylation reaction is demonstrated.Stavropol' State University, Stavropol' 355009. Russian Chemical Engineering University, Moscow 125190. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1099, August, 1997.     

7-alkyl-1,3,7-triazapyrenium salts: A rare case of double nucleophilic substitution

Russian Journal of General Chemistry -     

A new method for [c,d]pyridine peri-annelation: synthesis of azapyrenes from phenalenes and their dihydro derivatives

An effective synthesis of various azapyrenes from phenalenes and their dihydro derivatives has been developed using 1,3,5-triazines in polyphosphoric acid (PPA).