A Facile Preparation of Thioglycolurils from Glycolurils, and Regioselectivity in Thioglycoluril Template-Directed Crossed-Claisen Condensations

Journal of Organic Chemistry

Volumn 62, Issue 25, 1997, Pages 8834-8840

  Cow, Christopher N ^a   Harrison, Paul H M ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010349550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9713823     Document Type: Article

References (45)

1. The IUPAC name for glycoluril 2 is 1,2,5,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione; we have chosen to use the trivial name and the standard numbering system for glycolurils in which the bridgehead carbons are numbered 7 and 8 (see Scheme 1) rather than the 3a,6a numbering system that has also been used; the latter derives from the alternative imidazo[4,5-d]imidazoline nomenclature for glycolurils. We have chosen to use a system where N-3 and N-4 are the two methylated nitrogen atoms throughout, rather than N-1 and N-6. For the monothio derivatives, the numbering system has been chosen such that the relative priorities of the two exocyclic nitrogen substituent(s) always determine which nitrogen atom has highest priority, even though this sometimes opposes the numbering system based on preference for the thiocarbonyl over the carbonyl group (e.g. Scheme 2). Only when both substituents are identical does the thiocarbonyl group take precedence over the carbonyl for this numbering scheme (e.g. Scheme 1).
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