A facile one-pot protocol for the synthesis of tetrazolyl-tetrahydroisoquinolines via novel domino intramolecular cyclization/Ugi-azide sequence |
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| Affiliation: | 1. Department of Organic Chemistry, Saint Petersburg State University (SPbSU), Universitetsky pr., 26, Saint Petersburg 198504, Russia;2. Department of Chemistry, Lomonosov Moscow State University, Vorobievy Gory, 1, Moscow 119899, Russia;3. Department of Organic Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg 194021, Russia;1. Department of Medicinal Chemistry, GVK Biosciences Pvt. Ltd., Survey Nos: 125(part) & 126, IDA Mallapur, Hyderabad 500076, India;2. Division of Chemistry, Department of Sciences and Humanities, Vignan’s Foundation for Science, Technology and Research University (VFSTRU Vignans University), Vadlamudi, Guntur 522 213, AP, India;3. Shree Velagapudi Ramakrishna Memorial College (SVRMC-PG Studies), NAAC ''A'' Grade & ISO 9001:2015 Certified, (Autonomous), Nagaram 522 268 Guntur District, Andhra Pradesh, India;4. MCETRC, Tenali 522 201 Guntur, AP, India |
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| Abstract: | A facile one-pot, four-component domino reaction between 2-(2-bromoethyl)benzaldehyde, isocyanide, amine, and azide for the synthesis of tetrazolyl-tetrahydroisoquinoline derivatives has been developed. The reaction sequence involves intramolecular replacement of halide by iminium nitrogen followed by Ugi-azide reaction. The reaction is catalyst/additive free and takes place under ambient conditions with short reaction times to furnish products in good to excellent yields. |
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| Keywords: | Tetrazole Tetrahydroisoquinoline Ugi-azide One-pot transformation |
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