Improved synthesis of 1,4,7-triazacyclononane

Details Improved synthesis of 1,4,7-triazacyclononane Improved synthesis of 1,4,7-triazacyclononane

1992-06-30

1994-02-08

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540465, C07D25502

Patent

active

052849449

ABSTRACT:
An improved process is described for obtaining triazacyclononanes, esepcially 1,4,7-trimethyl-1,4,7-triazacyclononame. The first step involves reacting diethylenetriamine (DET) with a sulfonylation agent to form a sulfonamidated DET, in an aqueous medium with an inorganic base. In a second step, but preferably within the same reactor vessel without isolating intermediates, the sulfonamidated DET aqueous mixture is contacted with an aprotic organic solvent in the presence of a cyclizing unit such as ethylene glycol ditosylate or ethylene dibromide, thereby resulting in a cyclized sulfonamidated triamine compound. Thereafter the protecting groups are removed and the amine is alkylated, preferably within a single reaction vessel without isolation of intermediates.

REFERENCES:
Zhana et al. Chemical Abstracts vol. 108, 1988, Abstract 94530w.
Organic Syntheses, 58, pp. 86-98 (1978).
Luk'yanenko et al, Zhurnal Organ. Khimii, 25, 8, pp. 1776-1784 (Dec. 30, 1989) with English translation pp. 1537-1544 (Aug. 1990).
Luk'yanenko et al, Zhurnal Organ. Khimii, 23 (3), pp. 660-662 (Jun. 3, 1986 with English translation pp. 598-599 (Mar. 1987).
Searle and Geue, Aust. J. Chem. 37, pp. 959-970 (1984).
Qian et al, Tetrahedron Letters, 31 (45), pp. 6469-6472 (1990).
Biernat and Luboch, Tetrahedron Letters, 40 (10), pp. 1927-1929 (1984).
Buttafava et al., Inorg. Chem., 25, pp. 1456-1461 (1986).
McAuley et al., Inorg. Chem., 23, pp. 1938-1943 (1984).
Schneider and Busch, Chem. Ber., 119, pp. 747-750 (1986).
Bogatsky et al, Communications, pp. 136-138 (Feb. 1984).
Chavez and Sherry, J. Org. Chem., 54, pp. 2990-2992 (1989).
Pilichowski et al, Tetrahedron Letters, 41 (10), at pp. 1961.

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