US EPA

7456480 

Journal Article 

Electrophilic Cyclization of o -Anisole- and o -Thioanisole-Substituted Ynamides: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes 

Kong, Y; Yu, L; Fu, L; Cao, J; Lai, G; Cui, Y; Hu, Z; Wang, G 

2013 

1 

Synthesis
ISSN: 0039-7881
EISSN: 1437-210X 

45 

14 

1975-1982 

English 

10.1055/s-0033-1338481 

A facile synthesis of 3-substituted 2-amidobenzofurans and 2-amidobenzothiophenes via electrophilic cyclization reaction of o-anisole- and o-thioanisole-substituted ynamides with I2, NBS and NCS was developed. The products 3-iodo-2-amidobenzofurans were further transferred into 3-aryl-, 3-alkynyl, and 3-vinyl-2-amidobenzofurans via Pd-catalyzed reactions such as Suzuki-Miyaura and Sonogashira cross-coupling reactions and the Heck reaction. © Georg Thieme Verlag Stuttgart, New York. 

2-amidobenzofurans; 2-amidobenzothiophenes; cross-coupling reaction; electrophilic cyclization; ynamide; 2-amidobenzofurans; 2-amidobenzothiophenes; Cross coupling reactions; Electrophilic cyclization; ynamide; Chemistry; Speech synthesis; Cyclization; 2 amidobenzofurans; 2 amidobenzofurans 2; 2 amidobenzothiophenes; 2 amidobenzothiophenes 4; 3 (3 bromobenzofuran 2 yl) 4 phenyloxazolidin 2 one; 3 (3 chlorobenzofuran 2 yl) 4 phenyloxazolidin 2 one; 3 (3 iodobenzofuran 2 yl) 4 phenyloxazolidin 2 one; 3 (5 bromo 3 iodobenzofuran 2 yl) 4 phenyloxazolidin 2 one; 3 [2 [2 (methylthio)phenyl]ethynyl] 4 phenyloxazolidin 2 one; 4 methyl n [2 [2 (methylthio)phenyl]ethynyl]n phenylbenzenesulfonamide; anisole derivative; benzofuran derivative; n (3 iodobenzofuran 2 yl) 4 methyl n phenylbenzenesulfonamide; n (3 iodobenzofuran 2 yl) 4 methyl n propylbenzenesulfonamide; n allyl n (3 bromobenzofuran 2 yl) 4 methylbenzenesulfonamide; n benzyl 4 methyl n (3 phenoxyprop 1 ynyl)benzenesulfonamide; n benzyl 4 methyl n (4 phenylbut 3 en 1 ynyl)benzenesulfonamide; n benzyl 4 methyl n [2 [2 (methylthio)phenyl]ethynyl]benzenesulfonamide; n benzyl n (3 bromobenzo[b]thiophen 2 yl) 4 methylbenzenesulfonamide; n benzyl n (3 bromobenzofuran 2 yl) 4 methylbenzenesulfonamide; n benzyl n (3 chlorobenzo[b]thiophen 2 yl) 4 methylbenzenesulfonamide; n benzyl n (3 chlorobenzofuran 2 yl) 4 methylbenzenesulfonamide; n benzyl n (3 iodobenzo[b]thiophen 2 yl) 4 methylbenzene sulfonamide; n benzyl n (3 iodobenzofuran 2 yl)methanesulfonamide; n benzyl n[2 (2 methoxyphenyl)ethynyl]methanesulfonamide; tert butyl benzyl (3 iodobenzofuran 2 yl)carbamate; tert butyl benzyl [2 (2 methoxyphenyl)ethynyl]carbamate; thioanisole; unclassified drug; ynamide derivative; article; carbon nuclear magnetic resonance; catalysis; chemical structure; cross coupling reaction; cyclization; electrophilicity; electrospray mass spectrometry; Heck reaction; high resolution melting analysis; proton nuclear magnetic resonance; Sonogashira reaction; Suzuki reaction; synthesis