Zur Constitution des Chinophtalons und der beiden isomeren Chinophtaline;

Abstract

Dipheiiylamiii mit Phtalsaureaiih~ &id. ' ) Rep. d. d e n t d i . cheni. Bes. 16, 513 und 1082. *) ~r i~-~t n i i t t l i e~l i~n~ des Herrn Prof. Dr. ci. S c 1111 1 t z. ' ) Ber. d. deutsch. chem. Ges. 16, 2602. 20 Annalen der Chemie 315. Bd.6, Uer. d. deutscli. chem. Ges. 16, 2472. ' ) C l a i s e n urid C r i s m e r , ciiese Annaleii 118, 129; K o m i i e n o s , ebeiida 118. 145, C 1 a i s e 11 nnd 11 a t 11 e w s , ebeiida 118, 170. ") loc. cit. ' ) Diesr Annnlen 303, 217. lo) Ber. (1. dentsch. cliem. Ges. 30, 1183. Ber. (1. dentsch, cliem. Ges. 33, 3175.u;1zd der beiden isomeren Clainophtaline.

The Chemistry of Quinolines.

“…Eibner and Lange (64) and Eibner and Hofmann (63) made an extensive investigation of the reaction of quinaldine with phthalic anhydride. On gently heating a mixture of these substances, there is first formed a compound (II) which when further heated loses water and yields quinoisophthalone (III).…”

The Last Fortress of Tin's Tyranny – Protodenitration of Nitroalkanes

“…Firstly, in 1978 Kornblum reported the displacement of the nitro group by hydrogen mediated by sodium thiomethoxide (29) at room temperature (Scheme 3). [7] As demonstrated on a range of substrates, the reactions 1901), [11] Balaban (1929), [12] Taivonen (1934), [13] Shriner (1938), [14] Salukaew (1951), [15] Adams (1952), [16] Hoffmann (1964), [17] Ginzburg (1964), [18] Masui (1965) [19] and Bavin (1966). [20] Scheme 2.…”

“…As a result, the research produced various novel transformations of nitro compounds, including unprecedented examples of protodenitration. The very first reported protodenitrations utilized readily available reducing agents such as sulfane (Eibner, 1901), [11] tin chloride (Balaban, 1929), [12] and sodium hydrogen sulfite (Taivonen, 1934), [13] producing derivatives 4-6 containing the carbonyl moiety (Figure 1). Later on, between 1938 and 1966, with more sophisticated reductants available, another set of substrates was denitrated using transition-metal catalysed hydrogenation (products 7, 11, and 13, Shriner 1938, Ginzburg 1964, and Bavin 1966), [14,18,20] metallic tin (8, Salukaew, 1951) [15] and sodium (10, Hoffmann, 1964), [17] lithium aluminum hydride (9, Adams, 1952) [16] and electrolysis (12, Masui 1965) [19] (Figure 1).…”

“… Early examples of substrate‐specific protodenitrations by Eibner (1901), [11] Balaban (1929), [12] Taivonen (1934), [13] Shriner (1938), [14] Salukaew (1951), [15] Adams (1952), [16] Hoffmann (1964), [17] Ginzburg (1964), [18] Masui (1965) [19] and Bavin (1966) [20] …”

Silica gel Catalyzed Synthesis of Quinophthalone Pigments Under Solvent-Free Conditions Using Microwave Irradiation

“…Their ability to act as ligands that form stable complexes with different cations is also well known [ 12 ]. Several methods for the preparation of quinophthalones have been reported such as treatment of phthalic anhydrides and a mixture of quinaldine with nitrobenzene [ 13 ], ZnCl 2 [ 14 , 15 , 16 , 17 ] or sodium hydride [ 18 ] and reactions of quinoline N-oxides/β-diketones [ 19 ]. Some of the methods mentioned above suffer from various drawbacks including long reaction times, low yield of products, difficult operating conditions and tedious work-up.…”