449778-84-1

Basic information

• Product Name: ETHYL 2-(4-METHYLPHENYL)-1-INDOLIZINECARBOXYLATE
• Synonyms: ETHYL 2-(4-METHYLPHENYL)-1-INDOLIZINECARBOXYLATE;ETHYL 2-(P-TOLYL)INDOLIZINE-1-CARBOXYLATE
• CAS NO: 449778-84-1
• Molecular Formula: C18H17NO2
• Molecular Weight: 279.33
• Mol File: 449778-84-1.mol

Chemical Properties

• Melting Point: 119-121°
• Appearance: /
• CAS DataBase Reference: ETHYL 2-(4-METHYLPHENYL)-1-INDOLIZINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-(4-METHYLPHENYL)-1-INDOLIZINECARBOXYLATE(449778-84-1)
• EPA Substance Registry System: ETHYL 2-(4-METHYLPHENYL)-1-INDOLIZINECARBOXYLATE(449778-84-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 449778-84-1(Hazardous Substances Data)

Upstream product

• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 
• 122-00-9 para-methylacetophenone 
• 2999-46-4 Ethyl isocyanoacetate 
• 17282-38-1 1-(4-methylphenacyl)pyridinium bromide 
• 110-86-1 pyridine 
• 619-41-0 4-(bromoacetyl)toluene 

Relevant articles and documents

Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines

An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonation/elimination/cycloisomerization is proposed.

Method for synthesizing indolizine compound under catalysis of silver

The invention discloses a method for synthesizing indolizine compounds under the catalysis of silver, which comprises the following steps of in an organic solvent system, stirring N-benzoylmethyl pyridinium bromide as shown in a formula (1) and an isocyanide compound as shown in a formula (2) according to a feeding molar ratio of 1: (1.2-2.0) in the presence of a metal silver salt as a catalyst to react in the air under an alkaline condition, and carrying out TLC tracking detection until the reaction is complete, and carrying out post-treatment on the reaction liquid to obtain the indolizine compound as shown in a formula (3). The method is easy to operate, raw materials and reagents are easy to obtain, reaction conditions are mild, a reaction system is environmentally friendly, products are easy to separate and purify, the yield reaches up to 91%, and the method is suitable for efficient and high-yield preparation of indolizine compounds and particularly suitable for synthesis of various 1, 2-substituted indolizine compounds. The method is suitable for large-scale industrial production, and has wide application prospects and important significance in organic synthesis.

Synthesis of Indolizines through Oxidative Linkage of C-C and C-N Bonds from 2-Pyridylacetates

Synthesis of indolizine-1-carboxylates through the Ortoleva-King reaction of 2-pyridylacetate followed by the Aldol condensation under mild reaction conditions has been described. This protocol is compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the regioselective formation of benzoyl-substituted indolizines through Michael addition followed by C-N bond formation, which are difficult to prepare by previous methods in a single step.