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Synthesis of Amino-Substituted α- and δ-Carbolines via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Ynamides.
Org Lett. 2019 03 01; 21(5):1331-1336.OL

Abstract

A metal-free [2 + 2 + 2] cycloaddition of alkyne-cyanamides or ynamide-nitriles with ynamides is described for the efficient synthesis of amino-substituted α- and δ-carbolines. This novel methodology is environmentally friendly and allows for highly regioselective access to carboline derivatives in good to excellent yields with wide functional group tolerance.

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Authors+Show Affiliations

Zhang J
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.
Guo M
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.
Chen Y
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.
Zhang S
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.
Wang XN
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.
Chang J
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education, School of Pharmaceutical Sciences, and College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou , Henan 450001 , P. R. China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30735400

Citation

Zhang, Jingyi, et al. "Synthesis of Amino-Substituted Α- and δ-Carbolines Via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles With Ynamides." Organic Letters, vol. 21, no. 5, 2019, pp. 1331-1336.
Zhang J, Guo M, Chen Y, et al. Synthesis of Amino-Substituted α- and δ-Carbolines via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Ynamides. Org Lett. 2019;21(5):1331-1336.
Zhang, J., Guo, M., Chen, Y., Zhang, S., Wang, X. N., & Chang, J. (2019). Synthesis of Amino-Substituted α- and δ-Carbolines via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Ynamides. Organic Letters, 21(5), 1331-1336. https://doi.org/10.1021/acs.orglett.9b00021
Zhang J, et al. Synthesis of Amino-Substituted Α- and δ-Carbolines Via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles With Ynamides. Org Lett. 2019 03 1;21(5):1331-1336. PubMed PMID: 30735400.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of Amino-Substituted α- and δ-Carbolines via Metal-Free [2 + 2 + 2] Cycloaddition of Functionalized Alkyne-Nitriles with Ynamides. AU - Zhang,Jingyi, AU - Guo,Meichao, AU - Chen,Yajuan, AU - Zhang,Shuangshuang, AU - Wang,Xiao-Na, AU - Chang,Junbiao, Y1 - 2019/02/08/ PY - 2019/2/9/pubmed PY - 2019/2/9/medline PY - 2019/2/9/entrez SP - 1331 EP - 1336 JF - Organic letters JO - Org Lett VL - 21 IS - 5 N2 - A metal-free [2 + 2 + 2] cycloaddition of alkyne-cyanamides or ynamide-nitriles with ynamides is described for the efficient synthesis of amino-substituted α- and δ-carbolines. This novel methodology is environmentally friendly and allows for highly regioselective access to carboline derivatives in good to excellent yields with wide functional group tolerance. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/30735400/Synthesis_of_Amino_Substituted_α__and_δ_Carbolines_via_Metal_Free_[2_+_2_+_2]_Cycloaddition_of_Functionalized_Alkyne_Nitriles_with_Ynamides_ DB - PRIME DP - Unbound Medicine ER -