A synthesis of N-bridged 5,6-bicylic pyridines via a mild cyclodehydration using the burgess reagent and discovery of a novel carbamylsulfonylation reaction.
Cyclodehydration using the Burgess reagent provided a novel approach toward the synthesis of N-bridged 5,6-bicylic pyridines including pyrolo-, imidazo-, and triazolopyridines under mild and neutral conditions. The methodology tolerates acid-sensitive functional groups. A novel addition product was observed between the resulting pyrrolo- or imidazopyridine and an additional equivalent of the Burgess reagent, producing the corresponding sulfonylcarbamate adduct.
Discovery Chemistry, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, Connecticut 06492, USA. jack.li@bms.com
Jie Jack
JJ
Li
James J
JJ
Li
Jun
J
Li
Ashok K
AK
Trehan
Henry S
HS
Wong
Subramanian
S
Krishnananthan
Lawrence J
LJ
Kennedy
Qi
Q
Gao
Alicia
A
Ng
Jeffrey A
JA
Robl
Balu
B
Balasubramanian
Bang-Chi
BC
Chen
D002219:Carbamates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D002219:Carbamates; D006574:Heterocyclic Compounds, 2-Ring; D011725:Pyridines; D013457:Sulfur Compounds; D014867:Water