Diversity-Oriented Synthesis of Functionalized 1-Aminopyrroles by Regioselective Zinc Chloride-Catalyzed, One-Pot ‘Conjugate Addition/Cyclization’ Reactions of 1,3-Bis(silyl enol ethers) with 1,2-Diaza-1,3-butadienes

2008 ◽  
Vol 350 (9) ◽  
pp. 1331-1336 ◽  
Author(s):  
Vahuni Karapetyan ◽  
Satenik Mkrtchyan ◽  
Andreas Schmidt ◽  
Orazio A. Attanasi ◽  
Gianfranco Favi ◽  
...  
Keyword(s):  
Zinc Chloride ◽  
Conjugate Addition ◽  
Cyclization Reactions ◽  
One Pot ◽  
Enol Ethers ◽  
Diversity Oriented Synthesis ◽  
Silyl Enol Ethers

scholarly journals One-Pot Synthesis of Silylated Enol Triflates from Silyl Enol Ethers for Cyclohexynes and 1,2-Cyclohexadienes

2018 ◽  
Vol 2018 (25) ◽  
pp. 3343-3347 ◽  
Author(s):  
Kazuki Inoue ◽  
Ryo Nakura ◽  
Kentaro Okano ◽  
Atsunori Mori
Keyword(s):  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
One Pot Synthesis

Synthesis of Chlorinated Arenes and Hetarenes by One-Pot Cyclizations of 1,3-Bis-silyl Enol Ethers

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 665-673 ◽  
Author(s):  
Peter Langer ◽  
Zahid Hassan
Keyword(s):  
Cost Effective ◽  
Coupling Reactions ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Cross Coupling Reactions ◽  
Silyl Enol Ether ◽  
Synthetic Routes ◽  
Metal Catalyzed ◽  
High Level

This account describes our recent findings and progress in synthesizing chlorinated arenes and hetarenes by one-pot cyclizations of 1,3-bis-silyl enol ether derivatives. These reactions allow for the preparation of highly functionalized products with a high level of regioselectivity. The synthetic routes are cost-effective avoiding additional functionalization steps. The products are difficult to be accessed by other methods. The chlorine atom is of relevance in medicinal and agriculture chemistry. In addition, it allows further functionalizations by transition-metal-catalyzed cross-coupling reactions.1 Introduction2 Cyclizations of 2-Chloro-1,3-bis(silyloxy)-1,3-butadienes2.1 3,5-Dihydroxychlorophthalates2.2 2,4-Dihydroxy-homochlorophthalates2.3 2-(Arylsulfonyl)chloropyridines2.4 1-Azaxanthones3 Cyclizations of 4-Chloro-1,3-bis(trimethylsilyloxy)-1,3-butadienes3.1 3-Chlorosalicylates3.2 Functionalized Chlorobiaryls3.3 3-Chloro-5-(2-chloroethyl)-salicylates3.4 2,4-Dihydroxychlorobenzophenones4 Cyclizations of 2-Chloro-3-(silyloxy)-2-en-1-ones4.1 Functionalized Chlorophenols4.2 Functionalized Chlorinated Biaryls and Chlorofluorenones4.3 Functionalized Chlorochromenones4.4 Functionalized 3-(Methylthio)chlorophenols4.5 Functionalized 3-Chloromethylphenols5 Conclusions6 List of Abbreviations

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