Sage Journals: Discover world-class research

Abstract

A new short synthesis of 7,9-dialkylcyclohepta[b]pyrimido[5,4-d]pyrrole-8(7H),10(9H)-dione derivatives consists of the reaction of 6-amino-1,3-dialkyluracils with tropone, 2-halotropones and 2,6-dibromotropone in an enamine-alkylation process, subsequent condensation of the amino group with carbonyl function, and aromatization under the reaction conditions.

References

Wamhoff

, Dzenis

and Hirota

, Adv. Heterocycl. Chem., 1992, 55, 129.

Yoneda

, Sakuma

, Mizumoto

and Ito

, J. Chem. Soc., Perkin Trans. 1, 1976, 1805.

Nishigaki

, Sato

, Shimizu

, Furukawa

, Sega

and Yoneda

, Chem. Pharm. Bull., 1980, 78, 142.

Ashton

W T.

and Brown

R. D.

, J. Heteracycl. Chem., 1980, 17, 1709.

Tominaga

, Okuda

; Tochiki

; Matsuda

and Kobayashi

, Heterocycles, 1981, 15, 679.

Yoneda

, Takayama

and Koshino

; Chem. Pharm. Bull., 1979, 77, 2507.

Nagamatsu

, Hashiguchi

, Higuchi

and Yoneda

, J. Chem. Soc., Chem. Commun., 1982, 1085.

Molina

, Vilaplana

M. J.

and Pastor

, Synthesis, 1992, 629.

Nitta

, Rev. Heteroatom Chem., 1993, 9, 87 and references therein.

10.

Nitta

, Mori

and Iino

, Heterocycles, 1991, 32, 23.

11.

Nitta

, Akie

and Iino

, J. Org. Chem., 1994, 59, 1309.

12.

Nitta

, Iino

, Mori

and Takayasu

, J. Chem. Soc., Perkin Trans. I, 1995, 1001.

13.

Nishiwaki

and Fukui

, J. Chem. Res., (S), 1986, 286; Nagahara

, Ieda

, Mimura

; Uchida

, Sato

and Okamura

, Eur. Pat. Appl., EP 376233, 1991 (Chem. Abstr., 1991, 1141, 23797b).

14.

Abe

, Matsuda

and Sugihara

, J. Heterocycl. Chem., 1996, 33, 1323.

15.

Papesch

and Schroeder

E. F

, J. Org. Chem., 1951, 16, 1879.

16.

Biggi

, Del Cima

and Pietra

, J. Am. Chem. Soc., 1973, 95, 7101; Pietra

, J. Chem. Soc., Chem. Commun., 1974, 544, and references therein.

17.

Takayasu

and Nitta

, J. Chem. Soc., Perkin Trans. I, 1997, 3255.

Studies on Pyrimidine-annulated Heterocycles: A New Short Synthesis of 7,9-Dialkylcyclohepta [b] pyrimido-[5,4- d ]pyrrole-8(7 H ),10(9 H )-dione Derivatives †

Abstract

References