𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Dense compounds of C, H, N, and O atoms: Nitramine derivatives of diimino- and dioxodecahydro-1 h,5h-diimidazo-[4,5-b:4′,5′-e]pyrazine

✍ Scribed by Murugappa Vedachalam; Vayalakkavoor T. Ramakrishnan; Joseph H. Boyer

Book ID
102846431
Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
518 KB
Volume
2
Category
Article
ISSN
1042-7163

No coin nor oath required. For personal study only.

✦ Synopsis

Guanidine condensed with I ,4-diformyl-2,3,5,6-tetrahydroxypiperazine 1 to give 2,6-diiminodecahydro-I H,5H-diimidazo[4,5-b:4',5'-e]pyrazine 3 isolated as the tetrahydrochloride salt. Nitric acid (1OWo) at -40°C converted the bisguanidine 3 to 2,6-dinitrimino-4,8dinitrodecahydro -IH,5Hdiimidazo[4,5b:4',5' -elpyrazine 8 isolated as a dihydrate, whereas nitration by nitronium tetrafluoroborate at 0" to 25°C afforded 2,6diimino -4,8dinitrodecahydro -I H,5Hdiimidazo[4,5-b:4',5'-e]pyrazine 9 isolated as the monohydrated bistetrafluoroborate salt, and treatment with nitric acid (100%) and acetic anhydride or phosphorus pentoxide converted the bisguanidine 3 to 2,6-dioxo-1,3,4,5,7,8-hexanitrodecahydro-l HSH-diimidazo[4,5-b:4',5'-e]pyrazine 4, also obtained from the tetra N-nitro compound 8 2 H 2 0 and from the dinitramine 9 e 2 HBF4 e HzO after similar treatment. The cis-syn-cis-configuration of the tricyclic bisurea 4 and bisguanidine 9 was confirmed by X-ray crystallographic analysis. Nitrosation by nitrous acid or by dinitrogen tetroxide converted the bisguanidine 3 to a hydrated 2,6-dinitrosimino-4,8-dinitrosodecahydro-1 H,SH-diimidazo[4,5-b:4',5'-e]pyrazine 10 2.5 HzO, whereas treatment with nitrosonium tetrafluoroborate afforded the bistetrafluoroborate salt of 4,8dinitroso derivative 11 2 HBF4. The nitrosamines 10 and 11 were converted to the tetranitro compound 8 2 HzO on treatment with nitric acid (100%) at _____ *To whom correspondence should be addressed.

-40°C. Treatment with fluoroboric acid etherate in acetonitrile converted nitroimino groups in compound 8 -2 H 2 0 and nitrosimino groups i n compound 10 2.5 HzO to imino groups i n compounds 9 2 HBF4 H 2 0 and 11 2 HBFl respectively.

📜 SIMILAR VOLUMES

2,6-Dithiodecahydro-1H,5H-Diimidazo[4,5,
2,6-Dithiodecahydro-1H,5H-Diimidazo[4,5,-b:4′,5′-e]Pyrazine and related dioxo- and diimino-decahydrodiimidazopyrazines
✍ Murugappa Vedachalam; Joseph H. Boyer 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 550 KB

## Abstract Thiourea condensed with 1,4‐diformyl‐2,3,5,6‐tetrahydroxypiperazine __2__ in the presence of hydrochloric acid to give 2,6‐dithiodecahydro‐1 H,5H‐diimidazo[4,5,‐b:4′,5′‐e]pyrazine __5__ isolated as the dihydrochloride salt. The salt __5__. 2HCl was converted to the free base __5__ by li

Dense compounds of C, H, N, and O atoms:
Dense compounds of C, H, N, and O atoms: II [1]. Nitramine and nitrosamine derivatives of 2-oxo- and 2-iminooctahydroimidazo-[4,5-d]imidazole
✍ Vayalakkavoor T. Ramakrishnan; Murugappa Vedachalam; Joseph H. Boyer 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 428 KB

The 4,6-dinitroso derivative 11 was obtained (83%) by the nitrosation of 2-oxooctahydroimidazo [ 4,5-d]imidazole 1 as the dihydrochloride and was converted to the 4,6-dinitro derivative 12 [ 66%] by treatment with nitric acid (loo%, -40°C) and to the 1.4,6-trinitro derivative 13 (66%) and the I,3,4,