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In the preceding paper (1) it was shown that 1,3,5-hexatriene might serve as the basis of a general synthetic method for condensed ring compounds of angular construction, such as steroids, since it was possible to secure, as the principal product of its addition to a cyclohexene, a derivative of 1-vinyloctahydronaphthalene with the annular double bond probably in the 2,3-position. The utility of this intermediate in the synthesis of angular polycyclic compounds would depend on its ability to isomerize to a 1-vinyl-l-octalin which could then add a dienophile. Before the feasibility of this procedure could be tested, we had observed that a 1,5-diene-3-yne can add two molecules of dienophile to give a crystalline product and it has now been found that this addition proceeds in the manner required for the synthesis of compounds of the type sought. In 1933 Blomquist and Marvel (2) found that both 4,7-di-n-propyl-3,7-decadiene-5-yne and 6,9-dimethyl-5,9-tetradecadiene-7-yne added two moles of maleic anhydride in boiling xylene. Since the products of reaction did not crystallize, the solution in xylene was heated with aqueous alkali. Neutralization of the alkaline extract gave products with the composition RéCuHioOs but, as these were amorphous, no attempt was made to characterize them further.We have now heated 2,5-dimethyl-l, 5-hexadiene-3-yne (I) with maleic anhydride at 130°. From the reaction-mixture a crystalline product, CieHuOe, was isolated. If the two moles of maleic anhydride added one after the other in the manner of a Diels-Alder reaction, then III and IV would be the expected structures.2 The intermediate II has not been

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Rings by the Dienyne Double Addition Reaction 1311 bath at 140°for eight hours. The product was isolated as the free base by crystallization from 50% ethanol and water; yield, 2.0 g. (80%).Other Heterocyclic Substituted Aminoquinaldines.-4-Chloro-6-methoxyquinaldine (0.02 mole) was mixed well with 0.022 mole of the desired heterocyclic amine, i. e., 8aminoquinoline, 8-amino-6-methoxyquinoline, thionine (0.011 mole), and 5-aminoindazole. The reaction mixture in each case was heated in an oil-bath at 160-1750 for three hours. The products were isolated and purified by washing the residues with 5% sodium hydroxide then numerous crystallizations from 90% ethanol; yields, approximately 60 to 70%. Summary A. relatively simple and economical process for the preparation of basically substituted propylamines has been reported.4-Chloro-6-methoxyquinaldine has been condensed with a few basically substituted aliphatic amines and several heterocyclic amines to give the corresponding 4-substituted quinaldines.