Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

Alexander A Titov; Reza Samavati; Elena V Alexandrova; Tatiana N Borisova; Tuyet Anh Dang Thi; Van Tuyen Nguyen; Tuan Anh Le; Alexey V Varlamov; Erik V Van der Eycken; Leonid G Voskressensky

doi:10.3390/molecules23113010

Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes

Molecules. 2018 Nov 17;23(11):3010. doi: 10.3390/molecules23113010.

Authors

Affiliations

¹ Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. titov_aa@pfur.ru.
² Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. reza_nasa3@yahoo.com.
³ Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. elena-aleksandrova-00-lena@mail.ru.
⁴ Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. borisova_tn@pfur.ru.
⁵ Institute of Chemistry of Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi 100000, Vietnam. dangtuyetanh1201@gmail.com.
⁶ Institute of Chemistry of Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi 100000, Vietnam. ngvtuyen@hotmail.com.
⁷ Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi 100000, Vietnam. ngvtuyen@hotmail.com.
⁸ Faculty of Chemistry of VNU University of Science, 19 Le Thanh Tong, Hoan Kiem, Hanoi 100000, Vietnam. huschemical.lab@gmail.com.
⁹ Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. avarlamov@sci.pfu.edu.ru.
¹⁰ Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. erik.vandereycken@kuleuven.be.
¹¹ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, 3001 Leuven, Belgium. erik.vandereycken@kuleuven.be.
¹² Organic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198 Moscow, Russia. lvoskressensky@sci.pfu.edu.ru.

Abstract

1-(p-Methoxyphenyl)tetrazolyl-substituted 6,7-dimethoxy(6,7-methylenedioxy)-1,2,3,4-tetrahydroisoquinolines formed tetrazolyl-substituted azocines in high yields by using activated alkynes. Unsubstituted at 6,7,8-aromatic fragment 1-tetrazolylisoquinoline interacted in several pathways forming tetrazolyl-substituted azocines, 1-tetrazolyl-1-R-vinylisoquinolines and 3-azaspiro[5.5]undeca-1,7,9-triene.

Keywords: Stevens rearrangement; activated alkynes; cycle expansion; tetrazolyl benzazocines; tetrazolylisoquinolines.

MeSH terms

Alkynes / chemistry*
Crystallography, X-Ray
Models, Molecular
Molecular Conformation
Spectrum Analysis
Tetrahydroisoquinolines / chemical synthesis*
Tetrahydroisoquinolines / chemistry

Substances

Alkynes
Tetrahydroisoquinolines

Abstract

MeSH terms

Substances

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