An efficient route to 2-substituted N-(1-amino-3-methylpyrrol)amides by ring-opening cyclization of benzylidene- and alkylidenecyclopropylcarbaldehydes with hydrazides.
A convenient and efficient synthetic method for the construction of 2,3-disubstituted pyrrolamides in moderate to good yields is established. The in situ generated water significantly accelerates the reaction rate. A possible mechanism involving the cascade ring-opening and thermal-induced rearrangement to produce the five-membered ring is proposed.
Tang
Xiang-Ying
XY
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Shi
Min
M
D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000737:chemistry*; D003500:Cyclization; D006834:Hydrazines / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
D000447:Aldehydes; D000577:Amides; D001597:Benzylidene Compounds; D006834:Hydrazines; D011758:Pyrroles; C029424:hydrazine