1394827-53-2

Basic information

• Product Name: butyl 3-phenylindolizine-1-carboxylate
• Synonyms: butyl 3-phenylindolizine-1-carboxylate
• CAS NO: 1394827-53-2
• Molecular Weight: 293.365
• Mol File: 1394827-53-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: butyl 3-phenylindolizine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: butyl 3-phenylindolizine-1-carboxylate(1394827-53-2)
• EPA Substance Registry System: butyl 3-phenylindolizine-1-carboxylate(1394827-53-2)

Safety Data

• Hazardous Substances Data: 1394827-53-2(Hazardous Substances Data)

Upstream product

• 29488-94-6 pyridin-2-yl-acetic acid butyl ester 
• 536-74-3 phenylacetylene 
• 100-39-0 benzyl bromide 
• 110-86-1 pyridine 
• 141-32-2 acrylic acid n-butyl ester 
• 2589-31-3 N-benzylpyridinium bromide 
• 1200204-20-1 n-butyl indolizine-1-carboxylate 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

Metal-free synthesis of indolizines through oxidative C–C and C–N bond formations of C (sp3) –H bonds

Iodine catalyzed synthesis of indolizine-1-carboxylates through oxidative C–C and C–N bond formations by the reaction of 2-pyridyl acetates with alkynes and alkenes without metal, oxidant, and base. This procedure is compatible with a broad range of functional groups in both alkynes and alkenes with good yields. The reaction proceeds through a tandem C–C bond formation followed by an intramolecular cyclization.

Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines

Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.

Pd-Catalyzed C-3 functionalization of indolizines via C-H bond cleavage

New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C-H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc) 2 catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.