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Low-temperature 1H and 13C NMR spectra of N-substituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles

✍ Scribed by Alan R. Katritzky; Novruz G. Akhmedov; Evgeniy M. Myshakin; Akhilesh K. Verma; C. Dennis Hall

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 414 KB
Volume: 43
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1553

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✦ Synopsis

The temperature-dependent (1)H and (13)C NMR spectra of 2-(2-butynyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole (4) (as a representative example of 1-9) in CFCl(3) + CD(2)Cl(2) solution are described and discussed. Below 183 K, the hexahydropyrazine ring inversions become slow on the NMR time-scale and 4 exists in principle as two conformational diastereomers. In fact, only one was observed with the N-2 substituent in an equatorial position as shown by a low-temperature NOESY experiment. The energy barrier for conformational interchange was calculated from NMR data to be 8.3 kcal mol(-1) (1 kcal = 4.184 kJ), in agreement with quantum chemical calculations. Unambiguous assignments for all proton and carbon resonances of 1-9 were made using 1D (APT, DEPT, NOE difference) and 2D (COSY, NOESY, gHMQC, gHMBC) NMR techniques.

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