One-Pot Reaction Sequence: N-Acylation/Pictet–Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of β-Carboline Alkaloid Analogues

One-Pot Reaction Sequence: N-Acylation/Pictet–Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of β-Carboline Alkaloid Analogues Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2024, Volume: 89, Number: 5, Pages: 3065-3071 Pages count : 7 DOI: 10.1021/acs.joc.3c02533

Authors

Alekseeva Kseniya A. ¹ , Fedoseeva Milana A. ¹ , Bakhanovich Olga V. ^2,1 , Khrustalev Victor N. ^3,4 , Potkin Vladimir I. ⁵ , Zhou Hongwei ⁶ , Nikitina Eugenia V. ¹ , Zaytsev Vladimir P. ¹ , Zubkov Fedor I. ¹

Affiliations

1	Organic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
2	Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, Prague 166 10, Czech Republic
3	Inorganic Chemistry Department, Faculty of Science, RUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
4	N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences, Moscow 119991, Russia
5	Institute of Physical Organic Chemistry of National Academy of Sciences of Belarus, 13 Surganov Street, Minsk 220072, Belarus
6	Jiaxing University, 1 Jiahang Road, Jiaxing, Zhejiang 314001, China

One-pot synthesis of tetrahydro-β-carbolines, fused with an isoindole core, was proposed starting from maleic anhydride and azomethines easily available from tryptamines and 3-(hetaryl)acroleins. This sequence includes four key steps: an acylation of the aldimine with maleic anhydride, a Pictet–Spengler cyclization, an intramolecular Diels–Alder reaction, and a concluding [1,3]-H shift. As a result, six- or seven-nuclear alkaloid-like heterocyclic systems, containing a benzo[1,2]indolizino[8,7-b]indole fragment annulated with furan, thiophene, or pyrrole, are formed in a diastereoselective manner.

Alekseeva K.A. , Fedoseeva M.A. , Bakhanovich O.V. , Khrustalev V.N. , Potkin V.I. , Zhou H. , Nikitina E.V. , Zaytsev V.P. , Zubkov F.I.
One-Pot Reaction Sequence: N-Acylation/Pictet–Spengler Reaction/Intramolecular [4 + 2] Cycloaddition/Aromatization in the Synthesis of β-Carboline Alkaloid Analogues
Journal of Organic Chemistry. 2024. V.89. N5. P.3065-3071. DOI: 10.1021/acs.joc.3c02533 WOS Scopus OpenAlex

Web of science:	WOS:001179167400001
Scopus:	2-s2.0-85185581680
OpenAlex:	W4391836380

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