Methyl pyrrole-2-carboxylate

Metapone madagascarica M. new species W-PG Trail following Methyl pyrrole-2-carboxylate 140 [182]... 

Table 2 Difference of chemical shifts (AS, ppm) a of 31a and 8a carbons relative to carbons of furan and methyl pyrrole-2-carboxylate...

Positive sign denotes a downfield shift from furan and methyl pyrrole-2-carboxylate, respectively. Chemical shifts for furan are 143.6 (C-2), 110.4 (C-3) <1975CS211>, and for methyl pyrrole-2-carboxylate 122.0 (C-2), 115.1 (C-3) <1974JP21004>. 

Trail Pheromones. Tumlinson et al. (133) identified methyl 4-methyl pyrrole-2-carboxylate (XXXVT as the major trail pheromone of the ant, Atta texana. Another poison gland product, 3-butyl-5-methyloctahydroindolizine (XXXVI) has been reported to be the dominant releaser of trail following for workers of Monomorium pharaonls (134).In contrast to these cyclic releasers... 

Reversed-order addition is also applied in the alternative procedure for 1-methyl-pyrrole-2-carboxylic acid. In this way the chance of introduction of moisture is minimized. This method is generally applicable if the organometallic intermediate is... 

The Vilsmeier-H2iack reagent, a chloroiminium salt, is a weak electrophile. Therefore, the Vilsmeier-Haack reaction works better with electron-rich carbocycles and heterocycles. Since pyrrole is very electron-rich, the Vilsmeier-Haack reaction readily takes place. Formylation of methyl pyrrole-2-carboxylate was achieved using the Vilsmeier-Haack reaction. The mechanism is shown below. The resulting methyl 5-formylpyrrole-2-carboxylate, in turn, was converted into nonpeptidic analogues of neurotesin(8-13), which are potential treatment for neuropsychiatric diseases such as schizophrenia and Parkinson s disease. 

A similar tactic was employed in transforming methyl pyrrole-2-carboxylate into hepatitis C virus (HCV) helicase inhibitors. ... 

Insects detect pheromones in surprisingly small amounts. Thus, male Bombyx mori begin to react when air contains as little as 100 molecules of the female sex pheromone per cm 210). The trail pheromone of the leaf cutting ant Atta texana, methyl-4-methyl-pyrrole-2-carboxyl-ate (46) is perceived at a concentration of 0,08 pg/cm, that is 3.48 molecules/cm 240), about the same as that recorded for the trail pheromone cw-3-cw-6-/ran5-8-dodecatrien-l-ol of Reticulitermes virgin-icus termite workers (47) 241). 

Dubis and Grabowski examined conformational isomers of methyl pyrrole-2-carboxylate by IR and RHF calculations. In one of the eonformers they emphatically found no H... 0 BCP and could hence rule out an intramolecular... 

Riley, R. G., Silverstein, R. M., Carroll, B. and Carrol, R. (1974b) Methyl 4-methyl-pyrrole-2-carboxylate a volatile trail pheromone from the leaf-cutting ant, Atta cephalotes. J. Insect Physiol., 20, 651-4. 

Methyl pyrrole-2-carboxylate with isopropyl chloride and aluminium chloride gives 4-, 5-, and 4,5-di-isopropyl derivatives. Primary attack is probably at C(4), and most of the 5-isopropyl compound is likely to arise by rearrangement, which has been shown to occur . 

Irwin, W. J. and D.L. Wleeler. 1972. The reaction of methyl pyrrole-2-carboxylate with epoxides. Tetrahedron 28 1113-1121. 

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