SYNTHESIS OF 1-PHENYLTETRAHYDROISOQUINOLINE DERIVATIVES

Abstract

Among the natural tetrahydroisoquinoline alkaloids, there are two small groups: 1-arylisoquinolines (cryptostylines I-III from Cryptostylis erythroglossa) [1,2], which were synthesized along with numerous analogs by Sh.N. Zhurakulov et al. [3,4], and N-benzyltetrahydroisoquinolines. This work examines the reactivity of 1-phenyltetrahydroisoquinoline 3a,b with substituted benzaldehydes (4a,b). New N-benzyl and oxazoisoquinoline derivatives were obtained, and their structures and properties were studied. The structure of the obtained compounds was established on the basis of NMR and mass spectral data. The use of 3a leads only to N-benzyl products 5,6. In the case of 3b, a mixture of 7a and 7b is formed. Molecular masses were determined in Mass spectra were recorded in an Acquity® QDa™ TLC-MS spectrometer (Waters). TLC-MS m/z 400.5049 [M+H]+ (7a), TLC-MS m/z 508.4465 [M+ H]+ (7b), TLC-MS m/z 628.4893 [M+ H]+ (8).

References

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3. Sherzod N. Zhurakulov, Nilufar Z. Mamadalieva, Valentina I. Vinogradova, et.all. Chemistry Europe, 10 (33), e01526 (2025).
4. Sh. N. Zhurakulov, V. I. Vinogradova, M. G. Levkovich. (2013). Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs.Chemistry of Natural Compounds.[Crossref]

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