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通过金催化炔烃的分子内氢胺化反应合成功能化的3-吡咯并-[1,2,3-]喹喔啉

Synthesis of Functionalized 3-pyrrolo-[1,2,3-] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes.

作者信息

Iazzetti Antonia, Fabrizi Giancarlo, Goggiamani Antonella, Marrone Federico, Sferrazza Alessio, Ullah Karim

机构信息

Dipartimento di Scienze Biotecnologiche di Base, Cliniche Intensivologiche e Perioperatorie, Università Cattolica del Sacro Cuore, L.go Francesco Vito 1, 00168 Rome, Italy.

Policlinico Universitario 'A. Gemelli' Foundation-IRCCS, 00168 Rome, Italy.

出版信息

Molecules. 2023 Aug 2;28(15):5831. doi: 10.3390/molecules28155831.

DOI:10.3390/molecules28155831
PMID:37570801
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10421283/
Abstract

A gold-catalyzed protocol to obtain functionalized 3-pyrrolo [1,2,3-] quinoxalines from suitable substituted indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the isolation of title compounds with yields from good to high. A reaction mechanism has been proposed, and theoretical calculations have been provided to rationalize the final step of the hypothesized reaction mechanism. As quinoxaline-containing polycyclic compounds, this class of molecules may represent a valuable template in medicinal chemistry and material science.

摘要

已经提出了一种金催化的方法，用于从合适的取代吲哚中获得功能化的3-吡咯并[1,2,3-]喹喔啉。结果表明，温和的反应条件与包括卤素、烷氧基、氰基、酮和酯在内的不同官能团兼容，从而能够以良好到高的产率分离出目标化合物。已经提出了反应机理，并提供了理论计算以合理化假设反应机理的最后一步。作为含喹喔啉的多环化合物，这类分子可能在药物化学和材料科学中代表有价值的模板。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/45569276d09c/molecules-28-05831-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/f0ac8b2033db/molecules-28-05831-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/deab1b6c7450/molecules-28-05831-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/c0b7adc3fd87/molecules-28-05831-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/5f569c718a47/molecules-28-05831-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/960a06b8fed9/molecules-28-05831-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/d9d4f6beb3f3/molecules-28-05831-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/3cab2e50eb4a/molecules-28-05831-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/45569276d09c/molecules-28-05831-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/f0ac8b2033db/molecules-28-05831-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/deab1b6c7450/molecules-28-05831-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/c0b7adc3fd87/molecules-28-05831-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/5f569c718a47/molecules-28-05831-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/960a06b8fed9/molecules-28-05831-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/d9d4f6beb3f3/molecules-28-05831-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/3cab2e50eb4a/molecules-28-05831-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab38/10421283/45569276d09c/molecules-28-05831-sch004.jpg

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