1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles

Weber L, Schnieder M, Boese R, Bläser D (2001)
Journal of the Chemical Society. Dalton Transactions (4): 378-382.

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Abstract
Reaction of a pyridine carbaldimine 2-(BuN)-Bu-t=CHC5H4N 1a with a molar equivalent of boron tribromide afforded a bicyclic 1,3,2-diazaborolium bromide 2a as an orange solid, whereas 1a and the corresponding 2-(2,6-Me2C6H3)N=CHC5H4N 1b with two equivalents of boron trifluoride gave non-ionic yellow adducts 3a and 3b. The reduction of compounds 2a, 3a and 3b with an excess of sodium amalgam in a hexane slurry led to the formation of 1-X-2-R-1,2-dihydro[1,3,2]diazaborolo[1,5-a]pyridines 4 (X=Br; R=Bu-t), 5a (F; Bu-t) and 5b (F; 2,6-Me2C6H3) as yellow oils (4a, 5a) or a yellow wax (5b), respectively. Treatment of 4 with an excess of chlorotrimethylsilane caused a Br/Cl exchange to afford chloro derivative 6. The addition of a methyl group to the boron atom was effected by reaction of heterocycle 4 with methyllithium. The BCN derivative 8 resulted from treatment of 4 with silver cyanide. Reduction of 4 with lithium aluminium hydride gave the 1-hydro-derivative 9, whereas the (BSBu)-Bu-t compound was obtained from the reaction of 4 with (KSBu)-Bu-t. Compound 8 was subjected to an X-ray diffraction analysis.
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Weber L, Schnieder M, Boese R, Bläser D. 1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles. Journal of the Chemical Society. Dalton Transactions. 2001;(4):378-382.
Weber, L., Schnieder, M., Boese, R., & Bläser, D. (2001). 1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles. Journal of the Chemical Society. Dalton Transactions(4), 378-382.
Weber, L., Schnieder, M., Boese, R., and Bläser, D. (2001). 1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles. Journal of the Chemical Society. Dalton Transactions, 378-382.
Weber, L., et al., 2001. 1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles. Journal of the Chemical Society. Dalton Transactions, (4), p 378-382.
L. Weber, et al., “1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles”, Journal of the Chemical Society. Dalton Transactions, 2001, pp. 378-382.
Weber, L., Schnieder, M., Boese, R., Bläser, D.: 1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles. Journal of the Chemical Society. Dalton Transactions. 378-382 (2001).
Weber, Lothar, Schnieder, M., Boese, Roland, and Bläser, Dieter. “1,2-Dihydro[1,3,2]diazaborolo[1,5-a]pyridines: a novel class of heterocycles”. Journal of the Chemical Society. Dalton Transactions 4 (2001): 378-382.
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