Method of synthesis of vicinal diamines

Details Method of synthesis of vicinal diamines Method of synthesis of vicinal diamines

1987-10-05

1990-06-12

Sutto, Anton H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

564511, 564461, 564487, 558166, 558145, 558378, C07D20302

Patent

active

049334700

ABSTRACT:
A method is described for producing vicinal diamines comprising the steps of converting a compound, possessing a leaving group on a carbon atom interposed between carbon atoms containing amino groups, to an aziridine-containing compound and reacting the latter compound with a nucleophile to form a vicinal diamine. The compound chosen for the rearrangement reaction may be selected from a wide range of compounds, including those with halide, heteroatom and aryl substituents. The amino groups may be blocked or unblocked. A variety of functional groups, including those which extend the carbon backbone, may be incorporated via opening of the aziridine-containing compound by addition of a selected nuclepohile. Aziridine-containing compositions and vicinal diamine compositions are disclosed. Functionalized vicinal diamines have numerous uses, including as intermediates for radionuclide-chelating ligands for use in the diagnosis and therapy of cancer.

REFERENCES:
Harrison et al., Compendium of Organic Synthetic Methods, 1971, pp. 266-270.
Dermer et al., Ethlyenimine and Other Aziridines, 1969, pp. 206-222.
March, Advanced Organic Chemistry; Reactions, Mechanisms and Structures, 1968, p. 332.
Swift et al., Stereospecific Synthesis of cis and trans 1,2 Diaminocyclohexanes and Aliphatic Vicinal Diamines, J. of Org. Chem., 32(3) pp. 512-513.
D. S. Jones et al. "A Convenient Synthesis of Vicinal Diamines", Amer. Chem. SOc. Abstracts, 194th ACS National Meeting, New Orleans, Aug. 30-Sep. 4, 1987, Abstract No. 57.
G. Swift and D. Swern, "Stereospecific Syntheses of cis- and trans-1, 2-Diaminocyclohexanes and Alphatic Vicinal Diamines", The Journal of Organic Chemistry, vol. 32, No. 3, pp. 511-517, 1967.
H. Kohn and S.-H. Jung, "New Stereoselective Method for the Preparation of Vicinal Diamines from Olefins and Cyanamide", J. Am. Chem. Soc. 105: 4106-4108, 1983.
S.-H. Jung and H. Kohn, "Stereoselective Synthesis of Vicinal Diamines from Alkenes and Cyanamide", J. Am. Chem. Soc. 107: 2931-2943, 1985.
J. A. Deyrup, The Chemistry of Heterocyctic Compounds, vol. 42, "Small Ring Heterocycles", Part 1 (Aziridines et al.), A. Hassner, ed., Chapeter 1, John Wiley & Sons, N.Y., 1983.
W. E. Fristad et al., "Conversion of Alkenes to 1,2-Diazides and 1,2-Diamines", J. Org. Chem. 50: 3647-3649, 1985.
G. Swift and D. Swern, "Stereospecific Synthesis of erythro- and threo-9,10-Diaminooctadecanoic Acids and Derivatives", J. Organ. Chem. 31: 4226-4229, 1966.
Y. Ali and A. C. Richardson, "Nucleophilic Replacement Reactions of Sulphonate Esters. Part V. The Synthesis of Derivatives of 2,3,4,6-Tetra-amino-2,3,4,6-tetradeosy-D-Glucose", J. Chem. Soc. (C), pp. 320-329, 1969.
G. Fraenkel and P. Pramanik, "Efficient One-Step Synthesis of a Cis Vicinal Tertiary Diamine and Its Complexation to a Lithium Carbanion Salt", J. Organ. Chem. 49: 1314-1316, 1984.
H. Natsugari et al., "Stereocontrolled Synthesis of Unsaturated Vicinal Diamines from Diels-Alder Adducts of Sulfur Dioxide Bis(imides)", J. Am. Chem. Soc. 106: 7867-7872, 1984.
R. Labia and C. Morin, "Unambiguous Preparation of a N.alpha.N.beta. Chemodifferentiated .alpha.,.beta.-Diaminopropionic Ester Through Michael Addition onto a Dehydroalanine Derivative", J. Org. Chem. 51: 249-251, 1986.
C. D. Gutsche and G. C. Mei, "Association Phenomena. 7. Mixed Chelate and Comicellar Catalysis of Acetyl Phosphate `Olysis` Reactions", J. Am. Chem. Soc. 107: 7964-7967, 1985.
L. H. DeRiemer et al., "Bledta II: Synthesis of a New Tumor-Visualizing Derivative of CO(III)-Bleomycin", Journal of Labelled Compounds and Radiopharmaceuticals, vol. XVIII, No. 10, pp. 1517-1534, 1980.
S. Kasina et al., "Tissue Distribution Properties of Technetium-99m-Diamide-Dimercaptide Complexes and Potential Use as Renal Radiopharmaceuticals", Journal of Medical Chemistry, vol. 29, No. 10, pp. 1933-1940, 1986.

Affiliated with

Also associated with

Rating

Method of synthesis of vicinal diamines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of synthesis of vicinal diamines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of synthesis of vicinal diamines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-618199