This work reports the design of [1,3,4]thiadiazolo[3',2':1,2]imidazo[4,5-c]quinolines using a Pictet-Spengler reaction. The scope of the reaction was achieved from 6-(2-aminophenyl)imidazo[2,1-b][1,3,4]thiadiazole derivatives and available aldehydes. A wide range of aldehydes were employed to examine the scope of the cyclization. In parallel, a mechanism investigation was realized and showed a hydride transfer which led to a dismutation of the intermediate species. To complete this methodological study, a "sequential" oxidation/SNAr procedure was performed to achieve C-2 nucleophilic substitution using several amine types.

The “Journées Franco-Belges de Pharmacochimie” is a recognized annual meeting in organic and medicinal chemistry known for the quality of scientific exchange and conviviality. Young researchers were encouraged to present their work and share ideas with senior scientists. Abstracts of plenary lectures, oral communications, and posters presented during the meeting are collected in this report.

AbstractAmination of the heterocyclic skeleton is first carried out under conditions A).

This work reports the original synthesis of trisarylimidazo[2,1-b][1,3,4]thiadiazole derivatives using a C-H arylation process. The scope of the reaction demonstrated the critical importance of the electronic effects of each substituent on the efficiency of the reaction. In addition, a double efficient one-pot' functionalization at the C-2 and then at the C-5 positions of 2-bromo-6-arylimidazo[2,1-b][1,3,4]thiadiazole derivatives was achieved using a sequential Suzuki-Miyaura-C-H arylation cascade procedure.

ChemInformVolume 47, Issue 36 Heterocyclic Compounds ChemInform Abstract: Palladium-Catalyzed Direct Arylation of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles. Chloe Copin, Chloe Copin Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorNicolas Henry, Nicolas Henry Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorFrederic Buron, Frederic Buron Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorSylvain Routier, Sylvain Routier Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this author Chloe Copin, Chloe Copin Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorNicolas Henry, Nicolas Henry Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorFrederic Buron, Frederic Buron Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorSylvain Routier, Sylvain Routier Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this author First published: 18 August 2016 https://doi.org/10.1002/chin.201636164Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume47, Issue36August, 2016 RelatedInformation

A new and efficient palladium-catalyzed amination of imidazo[2,1-b][1,3,4]thiadiazole at the C-5 position under microwave irradiation is reported. The reactivity toward bromine release at the C-5 position was investigated, and palladium-catalyzed cross-coupling conditions were optimized. A wide range of amines was employed to examine the scope and limitations of the method. To complete this methodological study, the influence of the nature and the positions of additional imidazo[2,1-b][1,3,4]thiadiazole substitutions was investigated.

An original and efficient palladium-catalyzed amination of imidazo[2,1-b][1,3,4]thiadiazole is reported. The SNAr and Buchwald–Hartwig cross-coupling reactions were investigated to access C-2 aminated imidazo[1,2-b][1,3,4]thiadiazole derivatives. The reaction conditions were optimized under microwave irradiation, and a wide range of amines were used to determine the scope and limitations of the method. To complete this study, the palladium-catalyzed and SNAr amination reactions were compared to determine the best strategy. The X-ray crystallographic data of imidazo[2,1-b][1,3,4]thiadiazole derivative 20 was used to formally establish the structures of the products.

Highly substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized through successive cyclization and Suzuki–Miyaura cross-coupling reactions. The palladium-catalyzed coupling reaction was optimized and a wide range of boronic acids was used to evaluate the scope and limitations of the methodology. The final compounds were obtained in fair to very good yields and high compatibility with various chemical functions or (hetero)cycles was observed.

ChemInformVolume 43, Issue 41 Heterocyclic Compounds ChemInform Abstract: Synthesis of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles Through Cyclization and Suzuki—Miyaura Cross-Coupling Reactions. Chloe Copin, Chloe Copin Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorNicolas Henry, Nicolas Henry Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorFrederic Buron, Frederic Buron Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorSylvain Routier, Sylvain Routier Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this author Chloe Copin, Chloe Copin Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorNicolas Henry, Nicolas Henry Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorFrederic Buron, Frederic Buron Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this authorSylvain Routier, Sylvain Routier Inst. Chim. Org. Anal., CNRS, Univ. Orleans, F-45067 Orleans, Fr.Search for more papers by this author First published: 13 September 2012 https://doi.org/10.1002/chin.201241140Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume43, Issue41October 9, 2012 RelatedInformation

Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

AbstractCyclic urea derivatives are synthesized by carbonylation of primary and secondary diamines.