Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

J. R. Falck; Shuanhu Gao; Ravi Naga Prasad; Sreenivasulu Reddy Koduru

doi:10.1016/j.bmcl.2008.02.034

Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

J. R. Falck^*, Shuanhu Gao, Ravi Naga Prasad, Sreenivasulu Reddy Koduru

^*Corresponding author for this work

University of Texas Southwestern Medical Center

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

Electrophilic α-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. α-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.

Original language	English
Pages (from-to)	1768-1771
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2008.02.034
State	Published - 15 Mar 2008
Externally published	Yes

Keywords

Asymmetric
Enolate
Heterocycle
Thiazolidinedione
Thiocyanate

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10.1016/j.bmcl.2008.02.034

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title = "Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones",

abstract = "Electrophilic α-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. α-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.",

keywords = "Asymmetric, Enolate, Heterocycle, Thiazolidinedione, Thiocyanate",

author = "Falck, \{J. R.\} and Shuanhu Gao and Prasad, \{Ravi Naga\} and Koduru, \{Sreenivasulu Reddy\}",

year = "2008",

month = mar,

day = "15",

doi = "10.1016/j.bmcl.2008.02.034",

language = "英语",

volume = "18",

pages = "1768--1771",

journal = "Bioorganic and Medicinal Chemistry Letters",

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publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

AU - Falck, J. R.

AU - Gao, Shuanhu

AU - Prasad, Ravi Naga

AU - Koduru, Sreenivasulu Reddy

PY - 2008/3/15

Y1 - 2008/3/15

N2 - Electrophilic α-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. α-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.

AB - Electrophilic α-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. α-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.

KW - Asymmetric

KW - Enolate

KW - Heterocycle

KW - Thiazolidinedione

KW - Thiocyanate

UR - https://www.scopus.com/pages/publications/40949085205

U2 - 10.1016/j.bmcl.2008.02.034

DO - 10.1016/j.bmcl.2008.02.034

M3 - 文章

C2 - 18308568

AN - SCOPUS:40949085205

SN - 0960-894X

VL - 18

SP - 1768

EP - 1771

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

Abstract

Keywords

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