Dibenzodiaza-30-crown

Dibenzodiaza-21-crown-7 macrocycles, 421 Dibenzodiaza-30-crown-10 macrocycles, 405 table, 442... 

Table 8.7. Dibenzodiaza-crown Macrocycles with m-Benzo Groups. 445...

A bimolecular cyclic self-condensation of an A -hydroxyalkyl-o-fluo-robenzamide gave the dibenzodiaza-crowns in yields of 60-70% (method T-5). The amide nitrogen must be secondary for this reaction. A tertiary... 

Alkyl- or aryl-substituted amines also have been used to prepare the ben-zoaza-crowns. Pedersen and Bromels (1974, 1977) prepared a dibenzodiaza-crown by reacting a benzobis secondary amine with l,2-bis(2-tosyloxy-ethoxy)benzene followed by reductive removal of the benzyl groups (method U-6). 

The synthesis of a variety of dibenzodiaza-crowns from salicylaldehyde or its derivatives has been reported by Lindoy and coworkers (Adam et al., 1981a, 1981b Armstrong and Lindoy, 1975 Armstrong et al., 1977 Baldwin et al., 1987 Grimsley et al., 1977). The macrocycles were obtained via the corresponding diimines (Schiff bases), which were obtained by condensations of the appropriate dialdehydes and diamines as shown (method U-14). It was... 

A series of dibenzooxaaza macroeyeles have been prepared by a nontemplate cyclization of 1,5-diamino-3-pentanol and various bis-benzaldehyde compounds. The resulting cyclic bis Schiff base was reduced with sodium borohydride to give the dibenzodiaza-crowns in overall yields of 10-20%... 

A spontaneous self-condensation of an amine-substituted benzaldehyde takes place in high yield, at room temperature, and without regard to concentration or any other precautions that usually apply to macrocyclic condensation reactions (Martin et al., 1985). The hydroxymethyl substituent of the starting material was first oxidized to the aldehyde, which condensed with the primary amine of another molecule of starting material (method U-17). The resulting bis Schiff base was reduced to form the final dibenzodiaza-crown. 

A thiourea-containing dibenzodiaza-crown was prepared by treating 2,2 -diaminobenzyl ether with carbon disulfide using iodine as the catalyst (method V-11) (Glinka and Piatkowska, 1984). 

Lockhart and Thompson (1977) prepared a dibenzodiaza-crown by treating triglycolyl dichloride n = 2) with a bis(aromatic amine) followed by reduction (method V-12). This method, using the Stetter bis-amide synthesis for ring closure, has been used by others for the preparation of dibenzodiaza-crowns... 

Formanovskii and Murakhovskaya, 1985 Formanovskii et al., 1988, 1989 Markovich et al., 1983). Biernat and coworkers have prepared a series of dibenzodiaza-crowns by methods V-12 (above) and V-13 (below), except that some of their macrocycles contained propylene bridges and they used dichlorides as well as activated diacid derivatives as starting materials (Biernat and Luboch, 1984 Biernat et al., 1979). The bis-imidazolides shown in method... 

Both isophthaloyl dichloride and a,a -dibromo-m-xylene gave only dibenzodiaza-crowns, the 2 2 cyclization products, when treated with iV-substituted diethanolamine (method X-3) (He et al., 1986 Johnson et al., 1985 Zhang et al., 1983). 

TABLE 8.7. DIBENZODIAZA-CROWN MACROCYCLES WITH aw-BENZO GROUPS... 

Dibenzocyclam, 708 Dibenzodiaza-crown macrocycles complexation of, 12 preparation of, 402,404,405,406, 407,... 

Hdgberg and Cram (1975) and Biernat and Luboch (1984) prepared some dibenzodiaza-, triaza-, and tetraaza-crowns from a bis-tosylanilide derivative prepared from o-nitrophenol (method V-7). This procedure allows the synthesis of dibenzo-crowns containing from two to four nitrogen atoms de-... 

Dibenzodiaza-17-crown-5 macrocycles, 12 Dibenzodiaza-18-crown-5 macrocycles, 12 Dibenzodiaza-18-crown-6 macrocycles, 407, 409, 415, 418, 423... 

Dibenzodiaza-19-crown-5 macrocylcs, 12 Dibenzodiaza-20-crown-6 macrocycles, 402, 411... 

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