Reactions of 1-(2-Acetoxyethoxy)methyl-5-amino-4-cyanoimidazole with Isothiocyanates

The reactions of 1-(2-acetoxyethoxy)methyl-5-amino-4-cyanoimidazole (5) with isothiocyanates afforded 3-(2-acetoxyethoxy)methyl-5-(substituted amino)-7-(N-substituted thiocarbamoyl)-iminoimidazo[4, 5-d][1, 3]thiazine (6a-c) at 50°C in dimethylformamide. At more elevated temperature, for example, in...

Full description

Saved in:
Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 36; no. 4; pp. 1283 - 1288
Main Authors YAMADA, KEIKO, MORI, TAKEO, MATSUMOTO, HIROATSU, TAKEUCHI, TADAO, MIZUNO, YOSHIHISA, KANEKO, CHISATO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 25.04.1988
公益社団法人日本薬学会
Maruzen
Japan Science and Technology Agency
Subjects
acycloimidazole
antivial agent
Chemistry
Dimroth rearrangement
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
imidazo[4, 5-d][1, 3]thiazine
isothiocyanate
Organic chemistry
Preparations and properties
Sulfur nitrogen heterocycle
Five membered ring
Acyclic nucleoside
Temperature
Base catalysis
Organic dithiocarbamate
Nitrogen heterocycle
Guanidines
Thioureas
Hydroxyether
Carbon disulfide
Organic isothiocyanate
Bicyclic compound
Antiviral
Dimroth rearrangement
Online AccessGet full text
ISSN0009-2363
1347-5223
DOI10.1248/cpb.36.1283

Cover

More Information
Summary:The reactions of 1-(2-acetoxyethoxy)methyl-5-amino-4-cyanoimidazole (5) with isothiocyanates afforded 3-(2-acetoxyethoxy)methyl-5-(substituted amino)-7-(N-substituted thiocarbamoyl)-iminoimidazo[4, 5-d][1, 3]thiazine (6a-c) at 50°C in dimethylformamide. At more elevated temperature, for example, in refluxing pyridine, compound 5 reacted with methyl isothiocyanate to give 3-2(acetoxyethoxy)methyl-5-methylamino-7-(N-methylthiocarbamoyl)iminoimidazo[4, 5-d][1, 3]-thiazine (6b) and 9-(2-acetoxyethoxy)methyl-1-methyl-6-imino-2-thioxopurine (7b).On the other hand, when carbon disulfide was used in place of isothiocyanates, the reaction afforded 3-(2-acetoxyethoxy)methyl-7-imino-5-thioxoimidaxo]4, 5-d][1, 3]thiazine (8) in refluxing pyridine.Under alkaline conditions, 6 and 8 were found to be rearranged to 2-(substituted amino)-9-(2-hydroxyethoxy)methyl-6-thioxopurine (10) and 2, 6-dithioxo-9-(2-hydroxyethoxy)methylpurine (9), respectively.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.36.1283