Reactions of levulinic acid with norbornane/ene amino acids and diamines

G. Stájer, Angela E. Szabó, A. Csámpai, P. Sohár

Research output: Article

8 Citations (Scopus)

Abstract

Whereas the cyclizations of di-endo-3-aminobicyclo-[2.2.1]heptane-2- carboxylic acid (2) and di-endo-3-amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (3) with 4-oxopentanoic acid (1) yield methanodioxopyrrolo[1,2-a][3,1] benzoxazines 6 and 7, the di-exo analogues give either the pyrrolo[1,2-a] pyridine 8 as sole product (in the case of 4), or 10 together with the methyl-substituted derivative 9 (in the case of 5). Compound 1 reacts with di-exo-3-aminobicyclo[2.2.1]heptane-2-methanamine (11) and di-exo-3- aminobicyclo[2.2.1]hept-5-ene-2-methanamine (12) to give the methylene-bridged pyrrolo[2,1-b]quinazolinones 13 and 14 respectively; a pentacyclic product containing a dipyrrolodiazepine moiety 15 was also isolated. The structures and stereochemistry were elucidated by means of IR and NMR spectroscopy, including COSY, DIFFNOE, DEPT, HMQC and HMBC techniques.

Original languageEnglish
Pages (from-to)1318-1322
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
Publication statusPublished - márc. 12 2004

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Norbornanes
Heptanes
Diamines
Carboxylic Acids
Benzoxazines
Quinazolinones
Amino Acids
Stereochemistry
Cyclization
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Magnetic Resonance Spectroscopy
Derivatives
levulinic acid
methylamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Reactions of levulinic acid with norbornane/ene amino acids and diamines",
abstract = "Whereas the cyclizations of di-endo-3-aminobicyclo-[2.2.1]heptane-2- carboxylic acid (2) and di-endo-3-amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (3) with 4-oxopentanoic acid (1) yield methanodioxopyrrolo[1,2-a][3,1] benzoxazines 6 and 7, the di-exo analogues give either the pyrrolo[1,2-a] pyridine 8 as sole product (in the case of 4), or 10 together with the methyl-substituted derivative 9 (in the case of 5). Compound 1 reacts with di-exo-3-aminobicyclo[2.2.1]heptane-2-methanamine (11) and di-exo-3- aminobicyclo[2.2.1]hept-5-ene-2-methanamine (12) to give the methylene-bridged pyrrolo[2,1-b]quinazolinones 13 and 14 respectively; a pentacyclic product containing a dipyrrolodiazepine moiety 15 was also isolated. The structures and stereochemistry were elucidated by means of IR and NMR spectroscopy, including COSY, DIFFNOE, DEPT, HMQC and HMBC techniques.",
keywords = "Cyclocondensations, Heterocycles, NMR spectroscopy, Norbornene, Pyrrolobenzoxazines",
author = "G. St{\'a}jer and Szab{\'o}, {Angela E.} and A. Cs{\'a}mpai and P. Soh{\'a}r",
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T1 - Reactions of levulinic acid with norbornane/ene amino acids and diamines

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2004/3/12

Y1 - 2004/3/12

N2 - Whereas the cyclizations of di-endo-3-aminobicyclo-[2.2.1]heptane-2- carboxylic acid (2) and di-endo-3-amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (3) with 4-oxopentanoic acid (1) yield methanodioxopyrrolo[1,2-a][3,1] benzoxazines 6 and 7, the di-exo analogues give either the pyrrolo[1,2-a] pyridine 8 as sole product (in the case of 4), or 10 together with the methyl-substituted derivative 9 (in the case of 5). Compound 1 reacts with di-exo-3-aminobicyclo[2.2.1]heptane-2-methanamine (11) and di-exo-3- aminobicyclo[2.2.1]hept-5-ene-2-methanamine (12) to give the methylene-bridged pyrrolo[2,1-b]quinazolinones 13 and 14 respectively; a pentacyclic product containing a dipyrrolodiazepine moiety 15 was also isolated. The structures and stereochemistry were elucidated by means of IR and NMR spectroscopy, including COSY, DIFFNOE, DEPT, HMQC and HMBC techniques.

AB - Whereas the cyclizations of di-endo-3-aminobicyclo-[2.2.1]heptane-2- carboxylic acid (2) and di-endo-3-amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (3) with 4-oxopentanoic acid (1) yield methanodioxopyrrolo[1,2-a][3,1] benzoxazines 6 and 7, the di-exo analogues give either the pyrrolo[1,2-a] pyridine 8 as sole product (in the case of 4), or 10 together with the methyl-substituted derivative 9 (in the case of 5). Compound 1 reacts with di-exo-3-aminobicyclo[2.2.1]heptane-2-methanamine (11) and di-exo-3- aminobicyclo[2.2.1]hept-5-ene-2-methanamine (12) to give the methylene-bridged pyrrolo[2,1-b]quinazolinones 13 and 14 respectively; a pentacyclic product containing a dipyrrolodiazepine moiety 15 was also isolated. The structures and stereochemistry were elucidated by means of IR and NMR spectroscopy, including COSY, DIFFNOE, DEPT, HMQC and HMBC techniques.

KW - Cyclocondensations

KW - Heterocycles

KW - NMR spectroscopy

KW - Norbornene

KW - Pyrrolobenzoxazines

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