TY - JOUR

T1 - Transformations of 5-(2-arylethynyl)-2-methyl-2H-tetrazoles under superelectrophilic activation

AU - Ryabukhin, D S

AU - Lisakova, A D

AU - Заливацкая, Анна Сергеевна

AU - Боярская, Ирина Алексеевна

AU - Старова, Галина Леонидовна

AU - Трифонов, Ростислав Евгеньевич

AU - Ostrovskii, V A

AU - Васильев, Александр Викторович

N1 - Funding Information: This work was supported by Russian Science Foundation (grant no. 17-73-10087 ) (synthesis of tetrazoles 3–6 ), and Russian Foundation for Basic Research (grant no. 15-03-02936-a ) (synthesis of tetrazoles 1, 2 ). Spectral studies were performed at Center for Magnetic Resonance, Center for Chemical Analysis and Materials, Research Center for X-ray Diffraction Studies of Saint Petersburg University (Saint Petersburg, Russia). Appendix A

PY - 2018/4/12

Y1 - 2018/4/12

N2 - Reaction of 5-arylethynyl-2-methyl-2H-tetrazoles (acetylene tetrazoles) with arenes under the action of Brønsted superacid CF 3SO 3H or acidic zeolite HUSY CBV-720 gives rise to E-/Z-5-(2,2-diarylethenyl)-2-methyl-2H-tetrazoles, as products of hydroarylation of acetylene bond, in yields up to 98% with predominant formation of E-isomers. Cationic intermediates of these reactions have been studied theoretically by DFT calculations. Addition of CF 3SO 3H to the triple bond of acetylene tetrazoles leads to the corresponding E-/Z-vinyl triflates in high yields. Hydration of triple bond in these tetrazoles in H 2SO 4 results in the formation of 5-(2-aryl-2-oxoethyl)-2-methyl-2H-tetrazoles. Tandem hydroarylation-ionic hydrogenation of acetylene tetrazoles in the systems acid(CF 3SO 3H or AlCl 3)-arene-cyclohexane affords 5-(2,2-diarylethyl)-2-methyl-2H-tetrazoles.

AB - Reaction of 5-arylethynyl-2-methyl-2H-tetrazoles (acetylene tetrazoles) with arenes under the action of Brønsted superacid CF 3SO 3H or acidic zeolite HUSY CBV-720 gives rise to E-/Z-5-(2,2-diarylethenyl)-2-methyl-2H-tetrazoles, as products of hydroarylation of acetylene bond, in yields up to 98% with predominant formation of E-isomers. Cationic intermediates of these reactions have been studied theoretically by DFT calculations. Addition of CF 3SO 3H to the triple bond of acetylene tetrazoles leads to the corresponding E-/Z-vinyl triflates in high yields. Hydration of triple bond in these tetrazoles in H 2SO 4 results in the formation of 5-(2-aryl-2-oxoethyl)-2-methyl-2H-tetrazoles. Tandem hydroarylation-ionic hydrogenation of acetylene tetrazoles in the systems acid(CF 3SO 3H or AlCl 3)-arene-cyclohexane affords 5-(2,2-diarylethyl)-2-methyl-2H-tetrazoles.

KW - Acethylene tetrazoles

KW - Acidic zeolites

KW - Brønsted superacids

KW - Hydroarylation

KW - Ionic hydrogenation

KW - TETRAZOLES

KW - ANALOGS

KW - Bronsted superacids

KW - VINYL

KW - KETONES

KW - HYDROPHENYLATION

KW - CHEMISTRY

KW - ELECTROPHILICITY INDEX

KW - SYSTEMS

KW - DERIVATIVES

KW - HYDROARYLATION

UR - http://www.scopus.com/inward/record.url?scp=85042857688&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/transformations-52arylethynyl2methyl2htetrazoles-under-superelectrophilic-activation

U2 - 10.1016/j.tet.2018.02.050

DO - 10.1016/j.tet.2018.02.050

M3 - Article

VL - 74

SP - 1838

EP - 1849

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 15

ER -