Facile Synthesis of 2 H-Benzo[ h]Chromenes via an Arylamine-Catalyzed Mannich Cyclization Cascade Reaction

Yueteng Zhang; Peng Ji; Xiang Meng; Feng Gao; Fanxun Zeng; Wei Wang

doi:10.3390/molecules26123617

Facile Synthesis of 2 H-Benzo[ h]Chromenes via an Arylamine-Catalyzed Mannich Cyclization Cascade Reaction

Molecules. 2021 Jun 12;26(12):3617. doi: 10.3390/molecules26123617.

Authors

Yueteng Zhang^{1

2}, Peng Ji¹, Xiang Meng¹, Feng Gao¹, Fanxun Zeng¹, Wei Wang¹

Affiliations

¹ Departments of Pharmacology and Toxicology and Chemistry and Biochemistry, and BIO5 Institute, University of Arizona, Tucson, AZ 85721, USA.
² The School of Basic Medical Sciences, The Academy of Medical Science, Zhengzhou University, 100 Kexue Avenue, Zhengzhou 450001, China.

Abstract

A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes. The notable feature of the process included the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.

Keywords: aminocatalysis; cascade reaction; chromenes; organocatalysis; quinone methide.

Grants and funding

R01 GM125920/GM/NIGMS NIH HHS/United States