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Safe Synthesis of 4,7-Dibromo[1,2,5]thiadiazolo[3,4- d]pyridazine and Its S N Ar Reactions

Safe Synthesis of 4,7-Dibromo[1,2,5]thiadiazolo[3,4- d]pyridazine and Its S N Ar Reactions

Timofey N Chmovzh, Ekaterina A Knyazeva, Konstantin A Lyssenko, Vadim V Popov, Oleg A Rakitin

Molecules. 2018 Oct 9;23(10):2576.

PMID: 30304797

Abstract:

A safe and efficient synthesis of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine from the commercial diaminomaleonitrile is reported. Conditions for selective aromatic nucleophilic substitution of one or two bromine atoms by oxygen and nitrogen nucleophiles are found, whereas thiols formed the bis-derivatives only. Buchwald-Hartwig or Ullmann techniques are successful for incorporation of a weak nitrogen base, such as carbazole, into the [1,2,5]thiadiazolo[3,4-d]pyridazine core. The formation of rather stable S…η²-(N=N) bound chains in 4,7-bis(alkylthio)-[1,2,5]thiadiazolo[3,4-d]pyridines makes these compounds promising for the design of liquid crystals.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS779189	4,7-Dibromo-[1,2,5]thiadiazolo[3,4-c]pyridine			Price

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