Multicomponent One-Pot Synthesis of 3‑Tetrazolyl and 3‑Imidazo[1,2‑a]pyridin Tetrazolo[1,5‑a]quinolines

A series of 18 3-tetrazolyl-tetrazolo­[1,5-a]­quinolines were synthesized in 21–90% yields via a novel one-pot Ugi-azide/SNAr/ring–chain azido-tautomerization process. We report also the synthesis of 10 3-imidazo­[1,2-a]­pyridin-tetrazolo­[1,5-a]­quinolines in 28–94% yields via a novel one-pot Groeb...

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Published inJournal of organic chemistry Vol. 81; no. 21; pp. 10576 - 10583
Main Authors Unnamatla, M. V. Basavanag, Islas-Jácome, Alejandro, Quezada-Soto, Andrea, Ramírez-López, Sandra C, Flores-Álamo, Marcos, Gámez-Montaño, Rocío
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
UGI-AZIDE
BIS-HETEROCYCLIC COMPOUNDS
TETRAZOLES
RADICAL CYCLIZATION
CHEMISTRY
DIVERSITY
DERIVATIVES
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Summary:A series of 18 3-tetrazolyl-tetrazolo­[1,5-a]­quinolines were synthesized in 21–90% yields via a novel one-pot Ugi-azide/SNAr/ring–chain azido-tautomerization process. We report also the synthesis of 10 3-imidazo­[1,2-a]­pyridin-tetrazolo­[1,5-a]­quinolines in 28–94% yields via a novel one-pot Groebke–Blackburn–Bienaymé/SNAr/ring–chain azido-tautomerization process. Both synthetic strategies involve the use of microwaves or ultrasound, and catalyst-free conditions. Finally, we show the synthesis of the tetrazolo­[1,5-a]­quinoline-3-carbaldehyde and tetrazolo­[1,5-a]­quinoline-3-dimethyl acetal at room temperature in methanol as solvent.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01576