A Versatile Approach for the Synthesis of 8H-Thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-Acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and Its Derivatives: A Novel Synthesis of Intermediate (1-Acetyl-1H-indol-3-yl)malononitrile/cyanoacetates
Corresponding Author
Valeriya S. Velezheva
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
All-Russian Chemical Pharmaceutical Research Institute, 119815 Moscow, Russia
E-mail: [email protected] or [email protected]Search for more papers by this authorAlexander Yu. Lepyoshkin
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorKonstantin F. Turchin
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorIrina N. Fedorova
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorAlexander S. Peregudov
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorCorresponding Author
Patrick J. Brennan
Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, Colorado 80523-1682
E-mail: [email protected] or [email protected]Search for more papers by this authorCorresponding Author
Valeriya S. Velezheva
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
All-Russian Chemical Pharmaceutical Research Institute, 119815 Moscow, Russia
E-mail: [email protected] or [email protected]Search for more papers by this authorAlexander Yu. Lepyoshkin
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorKonstantin F. Turchin
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorIrina N. Fedorova
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorAlexander S. Peregudov
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 GSP-1 Moscow, Russia
Search for more papers by this authorCorresponding Author
Patrick J. Brennan
Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, Colorado 80523-1682
E-mail: [email protected] or [email protected]Search for more papers by this authorAbstract
We report on two approaches for the synthesis of new 2-amino-3-cyano/alkoxycarbonyl-8H-thieno[2,3-b]indoles 5 and another one for the synthesis of 2-N,N-dialkylamino-3-cyano/aryl-8H-thieno[2,3-b]indoles 16, based either on acetylindoxyl 1 and (1-acetyl-1H-indol-3-yl)malononitrile/cyanoacetates 14 or 2-bromoacetylindoxyl 2 transformations. A new, simple, rapid, and efficient method for the synthesis of valuable key intermediate malononitrile/cyanoacetates 14 based on acetylindoxyl 1 condensation with malononitrile or cyanoacetates in the presence of triethylamine has been developed. A number of synthetic procedures for the preparation of thioacetamides 6, 1-acetylthioisatin 8, and 2,2-disubstituted indoxyls 13 have been elaborated during the synthesis of thieno[2,3-b]indoles. Thioacetamides 6 have been shown as novel agents active against Mycobacterium tuberculosis H37Rv, the cause of tuberculosis, with minimal inhibitory concentration values ranging between 5 and 21 μg/mL.
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