Transition-metal-free synthesis of polysubstituted pyrrole derivatives via cyclization of methyl isocyanoacetate with aurone analogues

• Published in: Organic & biomolecular chemistry Vol. 16; no. 30; pp. 5422 - 5426
• Main Authors: Wang, Zhi-Peng, He, Yun, Shao, Pan-Lin
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2018; Royal Society of Chemistry
• Subjects: Atom economy; Chemistry; Chemistry, Organic; Physical Sciences; Pyrroles; Science & Technology; Sodium hydroxide; Synthesis; ASSISTED SYNTHESIS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; OLIGOSUBSTITUTED PYRROLES; ACID-CHLORIDES; 1,3-DIPOLAR CYCLOADDITION; ISOCYANIDES; REGIOSELECTIVE SYNTHESIS; CATALYZED REACTION; TETRASUBSTITUTED PYRROLES

Presented herein is an unprecedented transition-metal-free cyclization of methyl isocyanoacetate with aurone analogues catalyzed by NaOH. Various 2,3,4-trisubstituted pyrroles were obtained in excellent yields (up to 99%). The high efficiency of this synthetic procedure, coupled with the operational...