Journal
TETRAHEDRON
Volume 62, Issue 14, Pages 3309-3319Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2006.01.054
Keywords
hydrazides; structural identification; 1,2,3,9a-tetrahydroimidazo[1,2-a]indol-2(9H)-ones; hydrazines; oxadiazoles
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Heating 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolinium chloride in the presence of hydrazine bishydrate produces regioselectively the five-membered heterocycle 1-amino-1,2,3,9a-tetrahydro-9,9,9a-trimethylimidazo[1,2-a]indol-2(9H)-one. The assignment of the structure is based on extensive H-1, C-13 and N-15 NMR spectroscopic studies. No ring-chain tautomerism of the 1-amino-1,2,3,9atetrahydroimidazo[1,2-a]indol-2(9H)-one was observed to open-chain hydrazides or the corresponding six-membered 1,2,10,10a-tetrahydro[1,2,4]triazino[4,3-a]indol-3(4H)-one. Further transformations of 1-amino-1,2,3,9a-tetrahydroimidazo[1,2-a]indol-2(9H)-one were performed by treatment with aromatic aldehydes, acid chlorides and isocyanates giving access to 40 novel hydrazones, N,N'-diacylhydrazines, N-acyl-N'-carbamoylhydrazines and 1,3,4-oxadiazoles, (c) 2006 Elsevier Ltd. All rights reserved.
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