Home
Resources
Publications
Modified Guanidines as Potential Chiral Superbases. 3. Preparation Of 1,4,6-triazabicyclooctene Systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Guanidines With a Hydroxyethyl Substituent

Modified Guanidines as Potential Chiral Superbases. 3. Preparation Of 1,4,6-triazabicyclooctene Systems and 1,4-disubstituted 2-iminoimidazolidines by the 2-chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Guanidines With a Hydroxyethyl Substituent

T Isobe, K Fukuda, K Yamaguchi, H Seki, T Tokunaga, T Ishikawa

J Org Chem. 2000 Nov 17;65(23):7779-85.

PMID: 11073581

Abstract:

Simple preparation methods of modified guanidines have been explored as potential chiral superbases. Thus, 3,7,8-trisubstituted and 3,6,7, 8-tetrasubstituted 1,4,6-triazabicyclooctene systems were prepared from (1S,2S)-1,2-diphenylethylenediamine through stepwise 2-chloro-1, 3-dimethylimidazolinium chloride (DMC)-induced cyclizations of protected thioureas to the corresponding 2-iminoimidazolidines and then of 2-(2-hydroxyethylimino)imidazolidines to the bicyclic systems. Linear guanidines with a 2-hydroxyethyl functional group were prepared by the reaction of carbodiimides with 2-amino alcohols. Reaction of linear-type guanidines with DMC followed by base treatment afforded 1,4-disubstitued 2-iminoimidazolidines. Furthermore, another type of 1,4,6-triazabicyclooctene was also prepared through double DMC-induced cyclization of guanidines with two 2-hydroxyethyl substituents.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP29841698	(1S,2S)-(−)-1,2-Diphenylethylenediamine		29841-69-8	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: