Literature DB >> 18308568

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

J R Falck1, Shuanhu Gao, Ravi Naga Prasad, Sreenivasulu Reddy Koduru.   

Abstract

Electrophilic alpha-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. Alpha-thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18308568      PMCID： PMC2329916          DOI： 10.1016/j.bmcl.2008.02.034

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  8 in total

1.  New oxadiazolidinedione derivatives as potent and selective human beta3 agonists.

Authors:  B Hu; M Malamas; J Ellingboe; E Largis; S Han; R Mulvey; J Tillett
Journal:  Bioorg Med Chem Lett       Date:  2001-04-23       Impact factor: 2.823

2.  Thiazolidinediones for the treatment of type 2 diabetes.

Authors:  J W F Elte; J F Blicklé
Journal:  Eur J Intern Med       Date:  2007-01       Impact factor: 4.487

3.  Novel 5-substituted 2,4-thiazolidinedione and 2,4-oxazolidinedione derivatives as insulin sensitizers with antidiabetic activities.

Authors:  Yu Momose; Tsuyoshi Maekawa; Tohru Yamano; Mitsuru Kawada; Hiroyuki Odaka; Hitoshi Ikeda; Takashi Sohda
Journal:  J Med Chem       Date:  2002-03-28       Impact factor: 7.446

4.  Enantiomer ratio of MK-0767 in humans and nonclinical species.

Authors:  Zhongzhou Shen; Ray Bakhtiar; Masakatsu Komuro; Katsuya Awano; Fukutaro Taga; Adria Colletti; Don Hora; William Feeney; Susan Iliff; Ronald B Franklin; Stella Vincent
Journal:  Rapid Commun Mass Spectrom       Date:  2005       Impact factor: 2.419

5.  Studies on antidiabetic agents. VI. Asymmetric transformation of (+/-)-5-[4-(1-methylcyclohexylmethoxy)benzyl]-2,4- thiazolidinedione(ciglitazone) with optically active 1-phenylethylamines.

Authors:  T Sohda; K Mizuno; Y Kawamatsu
Journal:  Chem Pharm Bull (Tokyo)       Date:  1984-11       Impact factor: 1.645

Review 6.  Thiazolidinediones in dermatology.

Authors:  Alan S Boyd
Journal:  Int J Dermatol       Date:  2007-06       Impact factor: 2.736

Review 7.  Thiazolidinediones: novel treatments for cognitive deficits in mood disorders?

Authors:  Roger S McIntyre; Joanna K Soczynska; Hanna O Woldeyohannes; Gary F Lewis; Lawrence A Leiter; Glenda M MacQueen; Andrew Miranda; Don Fulgosi; Jakub Z Konarski; Sidney H Kennedy
Journal:  Expert Opin Pharmacother       Date:  2007-08       Impact factor: 3.889

8.  Studies on the racemization of a stereolabile 5-aryl-thiazolidinedione.

Authors:  Christopher J Welch; Michael H Kress; Maria Beconi; David J Mathre
Journal:  Chirality       Date:  2003-02       Impact factor: 2.437
  8 in total
  5 in total

1.  Lithium Hexamethyldisilazide-Mediated Enolization of Acylated Oxazolidinones: Solvent, Cosolvent, and Isotope Effects on Competing Monomer- and Dimer-Based Pathways.

Authors:  Gabriel J Reyes-Rodríguez; Russell F Algera; David B Collum
Journal:  J Am Chem Soc       Date:  2017-01-12       Impact factor: 15.419

2.  Structures and Reactivities of Sodiated Evans Enolates: Role of Solvation and Mixed Aggregation on the Stereochemistry and Mechanism of Alkylations.

Authors:  Zirong Zhang; David B Collum
Journal:  J Am Chem Soc       Date:  2018-12-17       Impact factor: 15.419

3.  Limited Chemical Structural Diversity Found to Modulate Thyroid Hormone Receptor in the Tox21 Chemical Library.

Authors:  Katie Paul-Friedman; Matt Martin; Kevin M Crofton; Chia-Wen Hsu; Srilatha Sakamuru; Jinghua Zhao; Menghang Xia; Ruili Huang; Diana A Stavreva; Vikas Soni; Lyuba Varticovski; Razi Raziuddin; Gordon L Hager; Keith A Houck
Journal:  Environ Health Perspect       Date:  2019-09-30       Impact factor: 9.031

4.  Ag/Pyridine Co-Mediated Oxidative Arylthiocyanation of Activated Alkenes.

Authors:  De-Long Kong; Jian-Xun Du; Wei-Ming Chu; Chun-Ying Ma; Jia-Yi Tao; Wen-Hua Feng
Journal:  Molecules       Date:  2018-10-22       Impact factor: 4.411

5.  Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles.

Authors:  Carlos R Gonçalves; Miran Lemmerer; Christopher J Teskey; Pauline Adler; Daniel Kaiser; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2019-11-12       Impact factor: 15.419
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.