- Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts
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Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist.
- Xiao, Ming-Yang,Chen, Zhen,Zhang, Fa-Guang,Ma, Jun-An
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supporting information
(2020/03/04)
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- Catalytic Direct Construction of Cyano-tetrazoles
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Cyano-tetrazole is the first reported compound that bears four nitrogen atoms in a single five-membered ring. This unique molecular scaffold has long been ignored after its discovery in 1885, mainly attributed to the scarcity of available synthetic methods. Indeed, the most popular approach to tetrazoles (that is the cycloaddition reaction between nitriles and azides) has inevitably excluded the possibility of introducing valuable cyano groups to decorate the final heterocyclic cores. Here, we describe a completely different disconnection strategy to the long time-pursued cyano-tetrazoles via a simple, direct, and practical cycloaddition transformation between readily accessible aryl diazonium salts and diazoacetonitrile. This method provides both regioisomers of disubstituted tetrazoles from the same set of starting materials in a metal cation controlled fashion.
- Ma, Jun-An,Peng, Xing,Xiao, Ming-Yang,Xue, Xiao-Song,Zhang, Fa-Guang,Zheng, Meng-Meng
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p. 7762 - 7767
(2020/10/09)
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- TETRAZOLE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted tetrazolyl, R2 is optionally substituted phenyl, optionally substituted pyridinyl or optionally substituted thienyl, and R3, R4, R5 and R6 are as defined herein. Also provided are methods of using the compounds for treating diseases associated with the P2X3 and/or a P2X2/3 receptor antagonist and methods of making the compounds.
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- THIAZOLE AND OXAZOLE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is a group of formula A or formula B, and X, R2, R3, R4, R5, R6, Ra and Rb are as defined herein. Also provided are methods of using the compounds for treating diseases mediated by a P2X3 and/or a P2X2/3 receptor antagonist and methods of making the subject compounds.
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- THIADIAZOLE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted thiadiazolyl, and R2, R3, R4, R5, R6, R7 and R8 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
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Page/Page column 21
(2010/06/22)
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- OXAZOLONE AND PYRROLIDINONE-SUBSTITUTED ARYLAMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Compounds of the formula 1: or a pharmaceutically acceptable salt thereof, wherein, X, Y, R1, R2, R3, R4, R5, R6 and R7 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
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Page/Page column 24-25
(2010/12/31)
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- BIPHENYL AND PHENYL-PYRIDINE AMIDES AS P2X3 AND P2X2/3 ANTAGONISTS
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted phenyl or optionally substituted pyridinyl, and R2, R3, R4, R5, R6, R7, R8 and R9 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
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Page/Page column 32
(2010/12/31)
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- Imidazole-substituted arylamides as P2X3 and P2X2/3 antagonists
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Compounds of the formula I: wherein R1 is optionally substituted imidazolyl, and R2, R3, R4, R5, R6, R7 and R8 are as defined herein. Also provided are methods of using the compounds for treating diseases mediated by a P2X3 and/or a P2X2/3 receptor antagonist and methods of making the subject compounds.
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Page/Page column 30
(2009/07/10)
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- Tetrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted tetrazolyl, R2 is optionally substituted phenyl, optionally substituted pyridinyl or optionally substituted thienyl, and R3, R4, R5, R6 R7 and R8 are as defined herein. Also provided are methods of using the compounds for treating diseases associated with the P2X3 and/or a P2X2/3 receptor antagonist and methods of making the compounds.
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Page/Page column 36
(2009/07/10)
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- Pyrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted pyrazolyl, and R2, R3, R4, R5, R6, R7 and R8 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
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Page/Page column 44-45
(2009/07/17)
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- Triazole-substituted arylamides as P2X3 and P2X2/3 antagonists
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted triazolyl, and R2, R3, R4, R5, R6, R7 and R8 are as defined herein. Also disclosed are methods of using the compounds for treating diseases associated with P2X3 and/or a P2X2/3 receptor antagonists and methods of making the compounds.
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Page/Page column 60-61
(2009/07/17)
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- Tetrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
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Compounds of the formula I: or a pharmaceutically acceptable salt thereof, wherein, R1 is optionally substituted tetrazolyl, R2 is optionally substituted phenyl, optionally substituted pyridinyl or optionally substituted thienyl, and R3, R4, R5 and R6 are as defined herein. Also provided are methods of using the compounds for treating diseases associated with the P2X3 and/or a P2X2/3 receptor antagonist and methods of making the compounds.
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Page/Page column 192
(2008/06/13)
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- THIAZOLE AND OXAZOLE-SUBSTITUTED ARYLAMIDES
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Compounds of the formula (I) or a pharmaceutically acceptable salt thereof, wherein: R1 is a group of formula A or formula B; and X, R2, R3, R4, R5, R6, Ra and Rb are as defined herein. Also provided are methods of using the compounds for treating diseases mediated by a P2X3 and/or a P2X2/3 receptor antagonist and methods of making the subject compounds.
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Page/Page column 52-53
(2008/12/05)
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