Abstract:
Di[1,2,3]triazolo[1,5-a:5’,1’-d][3,1,5]benzothiadiazepine treated with butyllithium undergoes ring opening via the thiophilic addition of butyllithium at the C–S bond, whereas 9,10-dihydrodi[1,2,3]triazolo[1,5-b:5’,1’-f][1,3,6]thiadiazepine mainly undergoes lithiation of the methylene group followed by C–N bond cleavage to give 1-vinyltriazolyl sulfide.
Document Type:
Article
Language: English
Citation:
N. N. Volkova, E. V. Tarasov, M. I. Kodess, W. Dehaen, V. A. Bakulev, “Ring opening in di[1,2,3]triazolo-[1,3,6]thiadiazepine and -[3,1,5]benzothiadiazepine in reactions with butyllithium”, Mendeleev Commun., 12:4 (2002), 131–132
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https://www.mathnet.ru/eng/mendc4128
https://www.mathnet.ru/eng/mendc/v12/i4/p131
This publication is cited in the following 7 articles:
S. M. Ivanov, “Rearrangements of polyaza(oxa-,thia-)heterocyclic carbanions in organic synthesis”, Russ Chem Bull, 70:4 (2021), 647
Davin Tan, Tomislav Friščić, “Carbodiimide insertion into sulfonimides: one-step route to azepine derivatives via a two-atom saccharin ring expansion”, Chem. Commun., 53:5 (2017), 901
O. I. Afanas´ev, O. A. Tsyplenkova, M. Yu. Seliverstov, S. E. Sosonyuk, M. V. Proskurnina, N. S. Zefirov, “Homocoupling of bromotriazole derivatives on metal complex catalysts”, Russ Chem Bull, 64:6 (2015), 1470
O.V. Denisko, Comprehensive Heterocyclic Chemistry III, 2008, 489
E. A. Shafran, V. A. Bakulev, Yu. A. Rozin, Yu. M. Shafran, “Condensed 1,2,3-triazoles (review)”, Chem Heterocycl Comp, 44:9 (2008), 1040
S. Hilton, S. Rossiter, Comprehensive Heterocyclic Chemistry III, 2008, 711
Natalya N. Volkova, Evgeniy V. Tarasov, Mikhail I. Kodess, Wim Dehaen, Vasiliy A. Bakulev, “Ring Opening in Di[1,2,3]triazolo‐[1,3,6]thiadiazepine and ‐[3,1,5]benzothiadiazepine in Reactions with Butyllithium.”, ChemInform, 34:4 (2003)
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