Large scale synthesis of twelve member diazamonocyclic compounds

Claim 2

A process for preparing a compound of formula I ##STR20## wherein a solvent solution of a compound of formula II ##STR21## is mixed with a solvent solution of a compound of formula III ##STR22## under suitable process conditions, wherein A, same or different, is N--R, O, S, CRR' or P(O)R, and R and R' are hydrogen, alkyl, alkylidene, aryl, tosyl, allyl or benzyl, and B is O.

Claim 3

The process of claim 1 wherein A is O and B is O.

Claim 4

The process of claim 1 wherein the compound of formula II--solvent solution and the compound of formula III--solvent solution are simultaneously added to a reaction vessel containing solvent.

Claim 5

The process of claim 3 wherein the reaction vessel solvent is benzene or toluene.

Claim 6

The process of claim 3 wherein the compound of formula II is concentrated in benzene in a range of between about 0.12M and about 0.17M.

Claim 7

The process of claim 5 wherein the solvent is benzene or toluene.

Claim 8

The process of claim 3 wherein the compound of formula III is concentrated in solvent in a range of between about 0.24M and about 0.34M.

Claim 9

The process of claim 7 wherein the solvent is benzene or toluene.

Claim 10

The process of claim 3 wherein addition of the compound of formula II--solvent solution is at a rate of between about 1.5 and about 2.5 ml per minute.

Claim 11

The process of claim 3 wherein addition of the compound of formula III--solvent solution is at a rate of between about 1.5 and about 2.5 ml per minute.

Claim 12

A process for preparing an azacorand of formula IV ##STR23## wherein K and L, same or different, are N--R, O, S, CRR', or P(O)R, and R and R' are hydrogen, alkyl, alkylidene, allyl, aryl, benzyl or tosyl, comprising: (a) forming the compound of formula I according to the process of claim 1; and (b) reducing the compound of step (a).

Claim 13

A compound of formula IV wherein K and L are not both O or S.

Claim 14

A compound of formula IV wherein K and L are not both O or S.

Claim 15

A process for preparing a chromogenic cryptahemispherand of formula V ##STR24## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl, aryl or benzyl; R', same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl, aryl or benzyl; R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl, aryl or benzyl; Y is an electron withdrawing group, e.g., CN NO 2 , CF 3 , COOR; m is 1 to 3; n is 1 to 3; a is 1 to 3; b is 1 to 3; k is 1 to 3; l is 1 to 3; and x is 2 to 4; wherein an azacorand formed as in claim 11 is coupled with the following compound VI ##STR25## wherein: R, same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, allyl, aryl or benzyl; R", same or different, is lower alkyl, lower alkylidene, lower alkenyl, allyl, aryl or benzyl; R", same or different, is hydrogen, lower alkyl, lower alkylidene, lower alkenyl, aryl or benzyl; Y is an electron withdrawing group; Z is halogen; and w is 2 to 4.