Method of preparing...

Details Method of preparing... Method of preparing...

2004-06-04

2010-02-09

Wilson, James O (Department: 1624)

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

Organic compounds

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

Reexamination Certificate

active

07659393

ABSTRACT:
A method of preparing cyclene having formula (I) from triethylenetetraamine having formula (VIII) or ethylenediamine having formula (VIII′) includes a series of steps. The first series of steps (I) includes a step A (one-pot preparation of the compound having formula (IIa) from the compound having formula (VIII)), followed by a step B (transforming the compound having formula (IIa) into cyclene having formula (I)). The second series of steps (II) includes a step C (preparing the compound having formula (IIb) from the compound having formula (VIII)), followed by a step D (transforming the compound having formula (IIb) into cylcene having formula (I)). The third series of steps (III) includes a step E involving the onepot preparation of the compound having formula (IIa) from the compound having formula (VIII), followed by a step B involving the transformation of the compound having formula (IIa) into cyclene having formula (I).

REFERENCES:
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patent: WO/03/029228 (2003-04-01), None
Boschetti et al. Chemical Communications, 2002, 312-313, available online Jan. 18, 2002.
Sandines; Rolf Wiggo et al: “A simple synthesis of the macrocycle 1,4,7,10-tetraazacyclododecane” ACTA Chemica Scandinavica, 53(12), 1402-1404, 1998, XP009025163 cited in the application p. 1403.
Herve, Gwenaelle et al: “A new route to cyclen, cyclam and homocyclen” Tetrahedron Letters, 39(38), 6861-6864, 1998, XP004132624 cited in the application p. 6863.
Hubin, Timothy J. et al: “:Synthesis and S-ray Crystal Structure Determination of the First Copper (II) Complexes of Tetraazamacrocycle-Glyoxal Condensates” Inorganic Chemistry, 41(26) 7006-7014, 2002, XP002269063 p. 7011.

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