Novel ring enlargement of lactams via quinazolinone annelation. A facile route to benzoannelated large-membered cyclic 1, 5-diamines

H Takeuchi, Y Matsushita, S Eguchi

Index: Takeuchi, Hisato; Matsushita, Yuji; Eguchi, Shoji Journal of Organic Chemistry, 1991 , vol. 56, # 4 p. 1535 - 1537

Full Text: HTML

Citation Number: 38

Abstract

A novel route to benzoannelated large-membered cyclic 1, 5-diamines from lactams is described. Thus, n-membered lactams 1 were N-acylated by o-azidobenzoyl chloride 5 to afford the corresponding imides 4. These were treated with tributylphosphine and underwent an intramolecular aza-Wittig reaction to give n-membered ring-fused quinazolinones 2 in 8446% yleld. By reductive cleavage of 2 with BH,. THF,(n+ 4)-membered cyclic diamines 3 ...

Related Articles:

Transition-metal complex-catalyzed reductive N-heterocyclization: synthesis of 4 (3H)-quinazolinone derivatives from N-(2-nitrobenzoyl) amides

[Akazome, Motohiro; Kondo, Teruyuki; Watanabe, Yoshihisa Journal of Organic Chemistry, 1993 , vol. 58, # 2 p. 310 - 312]

A facile synthesis of simple alkaloids—synthesis of 2, 3-polymethylene-4 (3H)-quinazolinones and related alkaloids

[Lee, Eung Seok; Park, Jae-Gyu; Jahng, Yurngdong Tetrahedron Letters, 2003 , vol. 44, # 9 p. 1883 - 1886]

One-pot synthesis of simple alkaloids: 2, 3-polymethylene-4 (3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine

[Jahng, Katherine Chae; Kim, Seung Ill; Kim, Dong Hyeon; Seo, Chang Seob; Son, Jong-Keun; Lee, Seung Ho; Lee, Eung Seok; Jahng, Yurngdong Chemical and Pharmaceutical Bulletin, 2008 , vol. 56, # 4 p. 607 - 609]

Nitrogen bridgehead compounds. 66. Bronchodilator nitrogen bridgehead compounds with a pyrimidinone moiety

[Hermecz, Istvan; Vasvari-Debreczy, Lelle; Horvath, Agnes; Balogh, Maria; Koekoesi, Jozsef; et al. Journal of Medicinal Chemistry, 1987 , vol. 30, # 9 p. 1543 - 1549]

More Articles...