N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIV.* Synthesis and Reactivity of the New Benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine Ring System
Dylan Innes A , Michael V. Perkins A , Andris J. Liepa B and Craig L. Francis B CA School of Chemical and Physical Sciences, Flinders University, Bedford Park, SA 5042, Australia.
B Biomedical Synthetic Chemistry Group, CSIRO, Ian Wark Laboratory, Clayton, Vic. 3168, Australia.
C Corresponding author. Email: craig.francis@csiro.au
Australian Journal of Chemistry 71(1) 58-69 https://doi.org/10.1071/CH17255
Submitted: 11 May 2017 Accepted: 15 August 2017 Published: 4 October 2017
Abstract
N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent regioselective reactions with the 1,3-NCC bis-nucleophilic 1H-benzimidazole-2-acetonitriles 4 and related compounds to produce benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine dioxides 6, 9, 12, and 14, representatives of a new ring system. Reaction of dichlorides 1 with trifluoroacetyl derivative 16 afforded benzo[4,5]imidazo[1,2-c]pyrimidines 19 and 20. An N-acyl and some N-alkyl derivatives of benzimidazo-thiadiazines 6 were prepared to demonstrate the potential of this new ring system as a novel scaffold for synthetic and medicinal chemistry applications. Treatment of the 4-cyano-5-methyl-benzimidazo-thiadiazine 26c with LiAlH4 resulted in an unexpected and remarkable conversion of the nitrile to give the 4,5-dimethyl-benzimidazo-thiadiazine 29.
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