The Synthesis Of Series Of Pyrrolo[2,3-c]azepine-4,8-diones | Posted on:2011-12-25 | Degree:Master | Type:Thesis | Country:China | Candidate:D D Li | Full Text:PDF | GTID:2121360305462596 | Subject:Physical chemistry | Abstract/Summary: | PDF Full Text Request | Pyrrole alkaloids is one of the important branches of alkaloid chemistry, many kinds of alkaloids which include pyrrole lactam cyclodione structural element show notalbe bioactivities, such as anti-bacterium, anticancer antivirus, et. al. Based on consulting literature, this thesis describe the synthesis of series of bioactivity substances 1-alkyl-6,7-dihydropyrrolo [2,3-c]azepine-4,8(1H,5H)-diones,N-(2-pyrrolecarbonyl)-β-alanine methyl esters(1A) and N-(2-cyanoethyl)-N-methyl-1H-pyrrole-2-carboxamide (1B) were synthesized as synthetic intermediates by refinement multi-step reactions including acylation, esterification, Michael addition, using the economic and convenient compouds such as pyrrole,β-alanine and acrylonitrile as starting materials. Inherited traditional methods, new idea was brought forth in synthetic method of the intermediates'alkylation.12 alkylation products (2a-21):N-(1-alkyl-2-pyrrolecarbonyl)-β-alanine methyl esters and N-(1-alkyl-2-cyanoethyl)-N-methyl-lH-pyrrole-2-carboxamide were facile synthesized by the nucleophilic substitution reaction using compounds (1A)& (1B) as reagents and RX as alkylates in the presence of anhydrous K2CO3 as alkaline catalyst, n-Bu4NBr (TBAB) as phase transfer catalyst in 68-91%yields, which avoid the preparation and use of 1-alkyl-2-(trichloroacetyl) pyrrol as synthetic intermediates.Then series of 1-alkyl-6,7-dihydropyrrolo-[2,3-c]azepine-4,8(1H,5H)-diones (4a-4f) were obtained in 65-77% yields through cyclocondensation of the corres-ponding acids (3a-3f) that came out from the hydrolysis of the 3-(1-alky 1-1H-pyrrole-2-carbonyl)aminopropionates (2a-2f) and the N-methyl-3-(1-alkyl-1H-pyrrole-2-carbonyl) aminopropionitriles (2k-21) in the presence of PPA-P2O5.Most of the above products prepared by the thesis are new compounds without document data existed for reference. All of the synthetic products were purified by crystallyzation or chromatography, and their structures were determined by means of 1HNMR, IR combination with the chemical & physical properties. Moreover, structures of some of these products were confirmed by single-crystal X-ray difraction. Reaction conditions and reaction mechanisms of the syntheses were discussed and explained in detail, and the spectral data also.
| Keywords/Search Tags: | 1-alkyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione, N-(1-alkyl-2 -pyrrolecarbonyl)-β-alanine esters, alkylation, cyclocondensation | PDF Full Text Request | Related items |
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