1999 Fiscal Year Final Research Report Summary
Studies on the selective synthesis of sulfur-containing Heterocycles by tandem conversion of functional group
| Project/Area Number |
10640509
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | University of Tsukuba |
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Principal Investigator |
NISHIO Takehiko University of Tsukuba Department of Chemistry, Professor, 化学系, 教授 (70089811)
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| Project Period (FY) |
1998 – 1999
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| Keywords | ω-Hydroxy Amides / ω-Keto Amides / Lawesson's Reagent / Thionation / N-Acylamino Alcohols / N-Acythreonines / Thiazines / Sulfur-Containing Heterocycles |
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| Research Abstract |
A facile synthesis of sulfur-containing heterocycles by the reaction of the substrates possessing multi-functional groups such as hydroxy, carbonyl and amide with Lawesson's reagent [2,4-bis(p-methoxyphenyl-1,3,2,4-dithiaphosphetane-2,4-disulfide (LR )] is described.
1. Treatment of ω-hydroxy amides with LR in toluene at reflux temperature gave thioenamides, mercapto amides, and sulfur-containing heterocycles, iminothiophene and dithiolactones depending on the number of methylene between hydroxy and amide groups.
2. Treatment of ω-keto amides with equiv. of LR under the same conditions gave the corresponding ω-keto amides, pyrroles, aminothiophenes, and thiopyranes.
3. Thiazine derivatives were obtained by the reaction of 3-N-acylamino alcohol with equiv. of LR. This reaction proceeds stereoselectively. Treatment of 3-N-acylamino alcohols with 0.5 equiv. of LR gave the corresponding N-acylamino thiols, which yielded thiazines by further treatment with 0.5 equiv. of LR.
4. Treatment od N-acylthreonines with LR yielded thiazolinones and oxazolinones.
From above results, the relative reactivity of the functional groups toward LR is considered to be hydroxy > amide > carbonyl > ester.
The reactions of the substrates possessing multi-functional groups with LR described here represent a useful method for the preparation of sulfur-containing heterocycles.
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Research Products
(11 results)
