96206-94-9

Upstream product

• 768-18-3 2-methylindolizine 
• 98-88-4 benzoyl chloride 
• 96206-84-7 1-(2-Oxo-2-phenyl-ethyl)-2-prop-1-ynyl-pyridinium; bromide 
• 3243-04-7 2-methyl-3-indolizinecarbonitrile 
• 110-86-1 pyridine 
• 6266-23-5 1-(carboxymethyl)pyridinium chloride 
• 40925-52-8 2-(prop-1-yn-1-yl)pyridine 
• 70-11-1 α-bromoacetophenone 
• 1620-53-7 1-phenyl-2-pyridin-2-ylethanone 
• 78-95-5 chloroacetone 

Downstream Products

• 929212-53-3 (1-benzoyl-2-methylindolizin-3-yl)oxoacetic acid methyl ester 

Relevant academic research and scientific papers

Methylenecyclopropane Ring Formation/Opening Cascade for the Synthesis of Indolizines

A unique strategy toward the synthesis of polysubstituted indolizines has been developed. When 2-pyridinyl-2-(2′-bromoallyl)-1-carboxylates were treated with Cs2CO3, the starting material went through a methylenecyclopropane ring formation/opening cascade, and the corresponding indolizines were obtained in moderate to good yield as a single regioisomer.

IMDOLIZINE DERIVATIVES AS LIGANDS OF THE CRTH2 RECEPTOR

Compounds of formula (I) are CRTH2 antagonists, useful in the treatment of, for example, asthma, chronic obstructive pulmonary disease, rhinitis, allergic airway syndrome, and allergic rhinobronchitis. Formula (I) wherein R1, R2. R3 and R4 each independently are hydrogen, C1-C6alkyl, fully or partially fluorinated C1-C6alkyl, halo, -S(O)nR10, -SO2N(R10)2, -N(R10)2, -C(O)N(R10)2, -NR10C(O)R9, -CO2R10, -C(O)R9, -NO2, -CN or -OR11; wherein each R9 is independently C1-C6alkyl, aryl, heteroaryl; R10 is independently hydrogen, C1-C6alkyl, aryl, or heteroaryl; R11 is hydrogen, C1-C6alkyl, fully or partially fluorinated C1-C6alkyl or a group -SO2R10 ; n is 0, 1 or 2; R5 is C1-C6alkyl, fully or partially fluorinated C1-C6alkyl, C1-C6alkenyl, C1-C6alkynyl, optionally substituted aryl, or optionally substituted heteroaryl; R6 is hydrogen, C1-C6alkyl or fully or partially fluorinated C1-C6alkyl ; R7 and R8 are independently hydrogen or C1-C6alkyl, or R7 and R8 together with the atom to which they are attached form a cycloalkyl group; and X is -CHR6-, -S(O)n-, -C(O)-, -NR6SO2- or -SO2NR6- wherein n is 0, 1 or 2.

Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis

1-Substituted indolizines with activity against Mycobacterium tuberculosis have been synthesized. The most active compounds carry an hydroxyphenylmethyl- or hydroxyalkyl substituent in the indolizine 1-position. The alkyl chain should be moderately long (C-5 or C-6). Aryl groups in the 2- and 3-position of the indolizine are also required. Removal of the 3-substituent resulted in significant loss of activity. A nitrile substituent in the 7-position is beneficial for both chemical stability and bioactivity. The compounds studied display a narrow antibacterial spectrum and appear to be quite selective antimycobacterial compounds. Moderate activity against certain pathogenic protozoa was also observed.

Structures and ambiphilic reactivities of indolizines. 5. Acylation of 2-methylindolizine

The acylation and carbomethoxylation of 2-methylindolizine were studied. In most cases minor amounts of the 1-substituted isomers were isolated in addition to the "usual" products of substitution in the 3 position. The data from the PMR and mass spectra of the 2-methyl-3- and 1-acylindolizines obtained are discussed.

Thermal Rearrangements of Cyclic Amine Ylides. VIII. Intramolecular Cyclization of 2-Ethynylpyridine N-Ylides into Indolizines and Cyclazines

Treatment of 6-unsubstituted 2-ethynyl-1-phenacylpyridinium bromides (10a-c) with 1,5-diazabicycloundec-5-ene in refluxing benzene resulted in cyclization to give the 3-benzoyl-indolizines (11) via the N-ylide intermediates 13, whereas heating the