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Efficient routes for the synthesis of 1,4,7,10,13-pentaazacyclohexadecane-14,16-dione


Da Pieve, Chiara; Medina-Molner, Alfredo; Spingler, Bernhard (2007). Efficient routes for the synthesis of 1,4,7,10,13-pentaazacyclohexadecane-14,16-dione. Synthesis, (5):679-682.

Abstract

The synthetic access to 1,4,7,10,13-pentaazacyclollexadecane-14,16-dione was significantly improved from an overall yield of 1% to 33%. The procedure involved the use of COCF, or DDE as highly selective protecting groups for primary amines and of Boc to protect the secondary amine functions. The reaction of a tris-Boc protected tetraethylenepentamine with malonic acid gave the macrocycle in a 44% yield, the same reaction with malonyl chloride, however, yielded only 3.6% of the desired product. Boc deprotection and removal of the trifluoroacetate salts gave access to the final product, 1,4,7,10,13-pentaazacyclohexadecane-14,16-dione, in an overall yield of 33%.

Abstract

The synthetic access to 1,4,7,10,13-pentaazacyclollexadecane-14,16-dione was significantly improved from an overall yield of 1% to 33%. The procedure involved the use of COCF, or DDE as highly selective protecting groups for primary amines and of Boc to protect the secondary amine functions. The reaction of a tris-Boc protected tetraethylenepentamine with malonic acid gave the macrocycle in a 44% yield, the same reaction with malonyl chloride, however, yielded only 3.6% of the desired product. Boc deprotection and removal of the trifluoroacetate salts gave access to the final product, 1,4,7,10,13-pentaazacyclohexadecane-14,16-dione, in an overall yield of 33%.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:March 2007
Deposited On:23 Oct 2012 12:27
Last Modified:05 Apr 2016 16:01
Publisher:Thieme
ISSN:0039-7881
Publisher DOI:https://doi.org/10.1055/s-2007-965924
Other Identification Number:ISI:000245009500006

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